Name: 5036-48-6|N-(3-Aminopropyl)-imidazole|97%
Brand: Ambeed
SKU: A342606
Price: 5.0 USD
Availability: InStock
Rating: 98 (27 reviews)

1
[ 5036-48-6 ]
[ 1918-79-2 ]
[ 95059-46-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	N-(3,4-dimethoxyphenethyl)benzo[b]thiophene-2-carboxamide (7) General procedure: A solution of compound 4b (0.4 g, 2.25 mmol),compound 3 (0.45 g, 2.47 mmol), HBTU (1.01 g, 2.69 mmol) and Et3N (0.48 mL, 3.37 mmol) in DMF (10 mL) was stirred at room temperature for 2 h.Then, the mixture was diluted with water (100 mL), and extracted with EtOAc (50mL × 3). The combined organic layers were dried over MgSO4, concentrated and purified by silica gel column chromatography (CH2Cl2: MeOH = 100:2) to give compound 7 (0.63 g, 73%) as a yellow solid, mp: 93-96 C.
	With water; 1,1'-carbonyldiimidazole 1.) THF, RT, 2 h, 2.) THF, a) RT, 18-24 h, b) reflux, 3-6 h; Yield given. Multistep reaction;

Reference： [1]Chen, Wei; Dong, Guoqiang; He, Shipeng; Xu, Tianying; Wang, Xia; Liu, Na; Zhang, Wannian; Miao, Chaoyu; Sheng, Chunquan [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 765 - 768]
[2]Press; Wright Jr.; Chan; Haug; Marsico; Tomcufcik [Journal of Medicinal Chemistry, 1987, vol. 30, # 6, p. 1036 - 1040]

2
[ 5036-48-6 ]
[ 496-41-3 ]
[ 95059-48-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	N-(3,4-dimethoxyphenethyl)benzo[b]thiophene-2-carboxamide (7) General procedure: A solution of compound 4b (0.4 g, 2.25 mmol),compound 3 (0.45 g, 2.47 mmol), HBTU (1.01 g, 2.69 mmol) and Et3N (0.48 mL, 3.37 mmol) in DMF (10 mL) was stirred at room temperature for 2 h.Then, the mixture was diluted with water (100 mL), and extracted with EtOAc (50mL × 3). The combined organic layers were dried over MgSO4, concentrated and purified by silica gel column chromatography (CH2Cl2: MeOH = 100:2) to give compound 7 (0.63 g, 73%) as a yellow solid, mp: 93-96 C.
	With water; 1,1'-carbonyldiimidazole 1.) DMF, RT, 2 h, 2.) DMF, a) RT, 18-24 h, b) reflux, 3-6 h; Yield given. Multistep reaction;

Reference： [1]Chen, Wei; Dong, Guoqiang; He, Shipeng; Xu, Tianying; Wang, Xia; Liu, Na; Zhang, Wannian; Miao, Chaoyu; Sheng, Chunquan [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 765 - 768]
[2]Press; Wright Jr.; Chan; Haug; Marsico; Tomcufcik [Journal of Medicinal Chemistry, 1987, vol. 30, # 6, p. 1036 - 1040]

3
[ 5036-48-6 ]
[ 3885-38-9 ]
2-<N-(3-(1-imidazolyl)propyl)carbamoyl>-3-methylquinoxaline [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 33 - 38

4
[ 5036-48-6 ]
[ 4291-63-8 ]
[ 136834-45-2 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 215 - 218

5
[ 5036-48-6 ]
[ 6324-10-3 ]
[ 95059-47-5 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 1036 - 1040

6
[ 5036-48-6 ]
[ 91-40-7 ]
[ 17134-17-7 ]
3-(3-Imidazol-1-yl-propyl)-1-phenyl-1H-quinazoline-2,4-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1483 - 1486

7
[ 104-53-0 ]
[ 67-56-1 ]
[ 5036-48-6 ]
[ 141871-02-5 ]
resin-bound isonitrile [ No CAS ]
2-[[2-(tert-Butoxycarbonyl-methyl-amino)-benzoyl]-(3-imidazol-1-yl-propyl)-amino]-4-phenyl-butyric acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 7227 - 7230

8
[ 5036-48-6 ]
[ 1955-46-0 ]
[ 18704-37-5 ]
N-(3-imidazol-1-yl-propyl)-5-(quinoline-8-sulfonylamino)-isophthalamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1998,vol. 8,p. 187 - 205

9
[ 5036-48-6 ]
[ 1955-46-0 ]
4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonylX (X=OH or Cl) [ No CAS ]
N-(3-imidazol-1-yl-propyl)-5-[(4,7,7-trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carbonyl)-amino]-isophthalamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1998,vol. 8,p. 187 - 205

10
[ 5036-48-6 ]
[ 1955-46-0 ]
NH₂(CH₂)2COOX (X=OH or Cl) [ No CAS ]
5-(3-amino-propionylamino)-N-(3-imidazol-1-yl-propyl)-isophthalamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1998,vol. 8,p. 187 - 205

11
[ 5036-48-6 ]
[ 38675-10-4 ]
{(R)-1-Benzyl-2-[(S)-2-(3-imidazol-1-yl-propylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 45 - 49

12
[ 1121-60-4 ]
[ 5036-48-6 ]
3-(1H-imidazol-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: pyridine-2-carbaldehyde; 3-(1H-imidazol-1-yl)propan-1-amine In ethanol at 20℃; for 2.5h; Molecular sieve; Stage #2: With sodium tetrahydroborate In ethanol at 0 - 20℃;	3-(1H-imidazol-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine (3c) General procedure: To a solution of aldehyde 1, 2, 3, or 4 (1.21mmol) in absolute ethanol (12mL) was added the appropriate amine a (1-(pyridin-2-yl)methanamine), b (1-(furan-2-yl)methanamine), or c (3-(1H imidazol-1-yl)propan-1-amine) (1.45mmol) and 4 molecular sieves. The solution was stirred at room temperature for 2.5h and filtered to remove molecular sieves. Sodium borohydride (2.90mmol) was then added in small portion to the resulting ethanol solution at 0°C and the mixture allowed to return at room temperature and stirred overnight. Water (15mL) was added and the solution stirred for 15min before to be concentrated under reduced pressure. The aqueous layer was extracted with DCM (5×5mL), and the combined organic phase was washed with brine, dried with MgSO4, filtered, and evaporated to dryness. Purification by flash chromatography (DCM/MeOH/TEA, 98:1:1 to 90:9:1) yielded 1a (370mg, 90%), 2a (318mg, 78%), 1b (320mg, 70%), 2b (347mg, 76%), 3c (400mg, 99%), or 4c (400mg, 97%) according to the aldehyde and primary amine used. 1H NMR (400MHz, CDCl3) δ: 1.97 (p, J=6.8Hz, 2H), 2.64 (t, J=6.7Hz, 2H), 3.88 (s, 2H), 4.06 (t, J=6.9Hz, 2H), 6.91 (s, 1H), 7.04 (s, 1H), 7.18 (ddd, J=1.2, 4.9, 7.6Hz, 1H), 7.26 (d, J=7.8Hz, 1H), 7.47 (s, 1H), 7.65 (td, J=1.8, 7.7Hz, 1H), 8.56 (m, 1H). APCI-MS for C12H17N4 [M+H]+: 217.3m/z
97%	With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 48h;

Reference： [1]Ouellet, Charles; Maltais, René; Ouellet, Étienne; Barbeau, Xavier; Lagüe, Patrick; Poirier, Donald [European Journal of Medicinal Chemistry, 2016, vol. 119, p. 169 - 182]
[2]Walther, Martin; Wermann, Kurt; Lutsche, Marion; Guenther, Wolfgang; Goerls, Helmar; Anders, Ernst [Journal of Organic Chemistry, 2006, vol. 71, # 4, p. 1399 - 1406]

13
[ 5036-48-6 ]
[ 434-90-2 ]
[ 870997-80-1 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 15907 - 15915

14
[ 862821-16-7 ]
[ 5036-48-6 ]
[ 862821-17-8 ]

Yield	Reaction Conditions	Operation in experiment
59.3%		3.44 mmol of <strong>[862821-16-7]1-(3,4-dimethoxyphenyl)cyclopropanecarboxylic acid</strong>, 3.5 mmol of N-Methyl morpholine, and 3.5 mmol of isobutyl chloroformiat were dissolved in dry tetrahydrofurane and stirred for 15 min at -15 C. Then 3.5 mmol of 3-(1H-imidazol-1-yl)alkyl-1-amine was added and the mixture was allowed to warm to 0 C. and was stirred for 12 h. The solvent was removed under reduced pressure and the remaining oil was redissolved in chloroform. Then the organic layer was washed two times by means of a saturated aqueous solution of NaHCO3, then dried over Na2SO4 and the solvent was removed. Purification was performed by means of centrifugal forced chromatography using a chromatotron device (Harrison Research Ltd.) utilizing silica plates of a layer thickness of 2 mm, and a CHCl3/MeOH gradient as eluting system resulting in 0.671 g (59.3%) of N-(3-(1H-imidazol-1-yl)propyl)-1-(3,4-dimethoxyphenyl)cyclopropane-carboxamide.

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 664 - 677
[2]Patent: US2008/249083,2008,A1 .Location in patent: Page/Page column 41

15
[ 5036-48-6 ]
[ 615-20-3 ]
N-(3-(1H-imidazol-1-yl)propyl)benzo[d]thiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine In toluene at 130℃; for 12 - 24h; Heating / reflux;	5; 110 N-(3-(1H-imidazol-1-yl)propyl)benzo[d]thiazol-2-amine EXAMPLES 110-1121H-imidazole-1-propanamine was reacted with the corresponding 2-chlorobenzo[d] thiazole in toluol for 24 h at a temperature of 130° C. After removing the solvent and recristallization from methanol example 110-112 was yielded in an amount of 55-65%.; EXAMPLE 110N-(3-(1H-imidazol-1-yl)propyl)benzo[d]thiazol-2-amine1H NMR δ 1.95-2.15 (m, 2H), 3.25-3.35 (m, 2H), 4.0-4.1 (t, 2H), 6.9 (s, 1H), 6.95-7.05 (t, 1H), 7.15-7.2 (m, 2H), 7.35-7.4 (d, 1H), 7.60-7.70 (m, 2H), 8.0-8.1 (br s, 1H); MS m/z 259.4 (M+H), 191.3 (M-C3H3N2.)
8.6%	With triethylamine In butan-1-ol for 24h; Heating;

Reference： [1]Current Patent Assignee: VIVORYON THERAPEUTICS AG - US2008/249083, 2008, A1 Location in patent: Page/Page column 39; 41; 44
[2]Buchholz, Mirko; Heiser, Ulrich; Schilling, Stephan; Niestroj, André J.; Zunkel, Katrin; Demuth, Hans-Ulrich [Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 664 - 677]

16
[ 5036-48-6 ]
[ 50-00-0 ]
[ 131543-46-9 ]
[ 69506-85-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 4201 - 4208

17
[ 5036-48-6 ]
[ 3622-23-9 ]
N-(3-(1H-imidazol-1-yl)propyl)-6-chlorobenzo[d]thiazol-2-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 664 - 677

18
[ 5036-48-6 ]
[ 2605-14-3 ]
N-(3-(1H-imidazol-1-yl)propyl)-6-methoxybenzo[d]thiazol-2-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 664 - 677

19
[ 5036-48-6 ]
[ 1070-70-8 ]
polymer, Mw = 3180, PDI = 2.12; monomer(s): 1,4-butanediol diacrylate; 1-(3-aminopropyl)imidazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 8155 - 8156

20
[ 5036-48-6 ]
[ 13048-33-4 ]
polymer, Mw = 2110, PDI = 1.69; monomer(s): 1,6-hexanediol diacrylate; 1-(3-aminopropyl)imidazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 8155 - 8156

21
[ 5036-48-6 ]
[ 4074-88-8 ]
polymer, Mw = 1400, PDI = 1.4; monomer(s): acrylic acid 2-(2-acryloyloxy-ethoxy)-ethyl ester; 1-(3-aminopropyl)imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 45℃; for 120h;

Reference： [1]Lynn; Anderson; Putnam; Langer [Journal of the American Chemical Society, 2001, vol. 123, # 33, p. 8155 - 8156]

22
[ 5036-48-6 ]
[ 103-72-0 ]
1-[3-(1H-imidazol-1-yl)propyl]-3-phenylthiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In chloroform at 20℃; for 8h;	General procedure for the synthesis of 1-(3-(1H-imidazol-1-yl)propyl)-3-phenylthiourea Phenylisothiocyanate (15 g, 111.11 mmol) was dissolved in chloroform and equimolar amount of amine (13.89 g, 111.11 mmol) was added slowly at room temperature, and then refluxed for 8 h when precipitation of the product started.The precipitate was collected by filtration, washed with chloroform, and dried to afford product the title compound as white powder.The reaction mixture was poured on crushed ice and the separated solid product was filtered, washed with water, dried, and recrystallized from ethanol (95%). The crystals were purified by column chromatography using chloroform- methanol (4:1) as eluent to afford the title compound. The formation of title compound (Scheme) was confirmed by recording its FT-IR, 1H NMR, 13C NMR and HRMS spectra. 1H NMR and 13C NMR spectra were recorded on Bruker Avance II 400 NMR spectrometer at 400 MHz with DMSO as solvent ( Scheme 1 ).
95%	In acetonitrile at 20℃; Inert atmosphere;	3.2 Preparation ofILPs andTBILs By taking ionic liquid precursor ILP1 as an example.1-(3-Aminopropyl)imidazole (2.00 g, 16.0 mmol) wasmixed with 20 mL acetonitrile under an atmosphere ofdry nitrogen. To the stirring solution, phenyl isothiocyanate(2.38g, 17.6mmol) pre-dissolved in 10mL acetonitrilewas added dropwise. The above-mentioned solutionwas stirred overnight at room temperature. Slowly a whiteprecipitate separated, which was collected by filtrationand washed with acetonitrile (3 × 30mL). The precipitatewas then dried at 60 °C under vacuum overnight to obtainwhite solid ILP1. Yield: 3.95g (95%). 1H NMR (DMSO,600MHz): δ (ppm) 9.51 (br, 1H), 7.81 (br, 1H), 7.64 (s,1H), 7.39 (d, 2H), 7.32 (t, 2H), 7.19 (s, 1H), 7.11 (t, 1H),6.89 (s, 1H), 4.00 (t, 2H), 3.45 (br, 2H), 2.02-1.98 (m, 2H).13C NMR (DMSO, 150 MHz): δ (ppm) 180.99, 139.62,137.82, 129.29, 128.99, 124.83, 123.71, 119.91, 44.33,41.82, 30.65. FT-IR (KBr, cm-1): 3330, 3276, 3145-3005,2961, 2939, 1618, 1542, 1500, 1457, 1321, 1268, 1230,1082, 916, 828, 755, 706, 663, 632, 505. ESI-MS calcd forC13H16N4S260.11, found 261.12 [M+H]+.
75%	In ethanol for 2h; Heating;

Reference： [1]War, Javeed Ahmad; Jalaja; Mary, Y. Sheena; Panicker, C. Yohannan; Armaković, Stevan; Armaković, Sanja J.; Srivastava, Santosh Kumar; Van Alsenoy [Journal of Molecular Structure, 2017, vol. 1129, p. 72 - 85]
[2]Xu, Fei; Cheng, Weiguo; Yao, Xiaoqian; Sun, Jian; Sun, Wei; Zhang, Suojiang [Catalysis Letters, 2017, vol. 147, # 7, p. 1654 - 1664]
[3]Buchholz, Mirko; Heiser, Ulrich; Schilling, Stephan; Niestroj, André J.; Zunkel, Katrin; Demuth, Hans-Ulrich [Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 664 - 677]

23
[ 5036-48-6 ]
[ 3460-49-9 ]
1-(3-(1H-imidazol-1-yl)propyl)-3-(4-ethoxyphenyl)thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.9%	In ethanol for 2h; Heating;

Reference： [1]Buchholz, Mirko; Heiser, Ulrich; Schilling, Stephan; Niestroj, André J.; Zunkel, Katrin; Demuth, Hans-Ulrich [Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 664 - 677]

24
[ 5029-67-4 ]
[ 5036-48-6 ]
(3-imidazol-1-yl-propyl)-pyridin-2-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With 2-(2-methyl-1-oxopropane)cyclohexanone; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 14h;

Reference： [1]Shafir, Alexandr; Buchwald, Stephen L. [Journal of the American Chemical Society, 2006, vol. 128, # 27, p. 8742 - 8743]

25
[ 5036-48-6 ]
[ 959857-77-3 ]
2-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-N-(3-imidazol-1-yl-propyl)-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.85%	With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	107 2-[2-(4-adaman1an-l-yl-phenoxy)-acetyla^ To solution of 2-[2^4-adamantan-l-yl-phenoxy)-acetylamino]-isonicotinic acid (40 mg, 0.098 mmol), l-(3-aminopropyl)imidazole(24.65 mg, 0.196 mmol) and DMAP(24.06 mg, 0.196 mmol) in DMF was added PyBOP(102.4 mg, 0.196 mmol) at room temperature, and stirred. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The resultant crude product was purified by PLC (MeOH:MC=l:9) to afford 2-[2-(4-adamantan-l-yl-phenoxy)-acetylamino]- N-(3-imidazDle-l-yl-propyl)-isonicotinamide as a colorless solid (44.4 mg, 87.85% yield).1HNMR (DMSO-dfo 300 MHz) 10.66(1H, s, pyridine), 8,78(1H, t, J=5.55 Hz, pyrazole), 8.46(1H, d,J=4.8 Hz, pyridine), 8.41(1H, s, pyrazole), 7.83 (IH, brs, OCH2CONH), 7.49-7.46(1H, m, pyrazole), 7.27(3H, d, J=9.3 Hz, aromatic, pyridine), 7.0(1H, brs, CONHCH2), 6.89(2H, d, J=9.0 Hz, aromatic), 4.78(2H, s, OCH2),4.03(2H, t, J=7.05 Hz, N-CH2), 3.23(2H, q, J=6.3 Hz5 CONHCH2CH2), 2.03(3H, s, adamantyl), 1.96(2H, m,CH2CH2CH2), 1.82(6H, d, J=2.4 Hz, adamantyl), 1.71(6H, s, adamantyl).
87.85%	With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;
87.85%	With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	107 2-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-N-(3-imidazole-1-yl-propyl)-isonicotinamide To solution of 2-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-isonicotinic acid (40 mg, 0.098 mmol), 1-(3-aminopropyl)imidazole (24.65 mg, 0.196 mmol) and DMAP (24.06 mg, 0.196 mmol) in DMF was added PyBOP (102.4 mg, 0.196 mmol) at room temperature, and stirred. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The resultant crude product was purified by PLC (MeOH:MC=1:9) to afford 2-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-N-(3-imidazole-1-yl-propyl)-isonicotinamide as a colorless solid (44.4 mg, 87.85% yield). 1H NMR (DMSO-d6, 300 MHz) 10.66 (1H, s, pyridine), 8.78 (1H, t, J=5.55 Hz, pyrazole), 8.46 (1H, d, J=4.8H), pyridine), 8.41 (1H, s, pyrazole), 7.83 (1H, brs, OCH2CONH), 7.49-7.46 (1H, m, pyrazole), 7.27 (3H, d, J=9.3 Hz, aromatic, pyridine), 7.0 (1H, brs, CONHCH2), 6.89 (2H, d, J=9.0 Hz, aromatic), 4.78 (2H, s, OCH2), 4.03 (2H, t, J=7.05 Hz, N-CH2), 3.23 (2H, q, J=6.3 Hz, CONHCH2CH2), 2.03 (3H, s, adamantyl), 1.96 (2H, m, CH2CH2CH2), 1.82 (6H, d, J=2.4 Hz, adamantyl), 1.71 (6H, s, adamantyl).

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY - WO2008/4798, 2008, A1 Location in patent: Page/Page column 72; 73
[2]Boovanahalli, Shanthaveerappa K.; Jin, Xuejun; Jin, Yinglan; Kim, Jin Hwan; Dat, Nguyen Tien; Hong, Young-Soo; Lee, Jeong Hyung; Jung, Sang-Hun; Lee, Kyeong; Lee, Jung Joon [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6305 - 6310]
[3]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY - US2009/306078, 2009, A1 Location in patent: Page/Page column 49

26
[ 5036-48-6 ]
[ 171489-59-1 ]
(6R,12AR)-6-benzo[1,3]dioxol-5-yl-2-(3-imidazol-1-ylpropyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3222 - 3240
[2]Patent: US2003/225094,2003,A1 .Location in patent: Page 11

27
[ 5036-48-6 ]
[ 5955-72-6 ]
2-[3-[imidazo-1-yl]-propylamino]-5-nitro-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 5h;Heating / reflux;	[0635] A mixture of <strong>[5955-72-6]2-chloro-5-nitro-benzimidazole</strong> (985 mg, 5.0 mmole) and 1-(3-aminopropyl)-imidazole (1.8 mL, 3 eq) in toluene (15 mL) was heated at reflux for 5 hr. The reaction was partitioned between EtOAc and brine to give a precipitate that was collected by filtration. Flash chromatography of this material (silica gel; stepwise gradient elution with mixtures of DCM containing 1, 2, 3, . . . 10% MeOH) afforded 2-[3-[imidazo-1-yl]-propylamino]-5-nitro-benzimidazole (550 mg) as a solid. This material was combined with 10% Pd on charcoal (500 mg), suspended in EtOH, and stirred under a hydrogen atmosphere (balloon) overnight. Removal of the catalyst by filtration and the solvent under reduced pressure left the crude 5-amino-2-[3-imidazo-1-ylpropylamino]-benzimidazole as a solid. A portion of this material (77 mg, 0.30 mmole) was added to a mixture of 319A (99 mg, 1.0 eq), an aqueous solution of HCl (0.60 mL, 1.0 M, 2 eq) and n-BuOH (1.5 mL). This was heated in a sealed vial at 120 C. for 20 hr. After cooling to RT, 572 (HPLC retention time (YMC ODS S7 3×50 mm): 1.20 min) was isolated by preparative HPLC.

Reference： [1]Patent: US2004/54186,2004,A1 .Location in patent: Page 146

28
[ 5036-48-6 ]
copper(ll) sulfate pentahydrate [ No CAS ]
[ 128-93-8 ]
1-(3-imidazolylpropylamino)-4-methylaminoanthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one; water;	In a first step, 1-(3-imidazolylpropylamino)-4-methylaminoanthraquinone was prepared by heating for 9 hours on a boiling waterbath and with stirring, the mixture comprising 47.4 g (0.15 mol) of 1-bromo-4-methylaminoanthraquinone (RN 128-93-8), 56.3 g (0.45 mol) of 3-imidazol-1-ylpropylamine (RN 5036-48-6) and 3.0 g of copper sulphate pentahydrate, in 60 ml of 1-methyl-2-pyrrolidone. The mixture was then poured over 300 g of ice-cold water, the crystallized precipitate thus obtained was dewatered, the precipitate was made into a paste again in water and dried at 40 C. under vacuum over phosphoric anhydride. 45.1 g of dark blue crystals were obtained which, after purification by recrystallization from boiling 1,2-dimethoxyethane, melted at 140 C. (Kofler). The elemental analysis for C21H20N4O2 was:

Reference： [1]Patent: US6437149,2002,B1

29
[ 5036-48-6 ]
[ 29705-38-2 ]
[ 282730-50-1 ]

Yield	Reaction Conditions	Operation in experiment
		a 1st Stage: Synthesis of 2-{(2-Hydroxyethyl)(4-(3-(imidazol-1-yl)propylamino)-3-nitrophenyl)amino}ethanol. The procedure described in Example 7 (2nd stage) was used. From 29.3 g (0.12 mol) of <strong>[29705-38-2]2-((4-fluoro-3-nitrophenyl)(2-hydroxyethyl)amino)ethanol</strong> (RN 29705-38-2) and from 50.0 g (0.4 mol) of 3-(imidazol-1-yl)propylamine (RN 5036-48-6), 39.0 g of purple crystals were obtained, which crystals, after purification by recrystallization from refluxing 96 ethyl alcohol, melted at 141 C. (Kofler) and had an elemental analysis, calculated for C16H23N5O4, of:

Reference： [1]Patent: US6464731,2002,B1

30
[ 5036-48-6 ]
[ 5768-39-8 ]
N-[3-(1-imidazolyl)propyl]-2,3-methylenedioxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; triethylamine; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;	Example 11 Preparation of N-[3-(1-imidazolyl)propyl]-2,3-methylenedioxybenzamide (compound 11) Thionyl chloride (0.8 ml) and DMF (0.02 ml) were added to a solution of 2,3-methylenedioxybenzoic acid (1.22 g) in 1,2-dichloroethane (5 ml), and the mixture was heated under reflux in a nitrogen flow for an hour. The solvent was distilled off under reduced pressure. The residue was dissolved in methylene chloride (10 ml) and added dropwise to triethylamine (1.02 ml) and N-(3-aminopropyl)imidazole (0.63 g) in methylene chloride (10 ml) while cooling with ice, stirred in a nitrogen flow for an hour, then poured into water. The organic layer was washed with aqueous saturated sodium bicarbonate and brine, then dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was separated by silica gel column chromatography eluding with chloroform/methanol (19:1 by volume) to obtain the objective N-[3-(1-imidazolyl)propyl]-2,3-methylenedioxybenzamide (compound 11)(1.3 g, 65 %) as an oil. NMR delta (CDCl3): 2.06 (2H, tt), 3.41 (2H, dt), 3.99 (2H, t), 6.03 (2H, s), 6.91 (3H, m), 7.00 (2H, s), 7.47 (2H, m)

Reference： [1]Patent: EP652217,1995,A1

31
[ 5036-48-6 ]
[ 24424-99-5 ]
[ 279238-29-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	In acetonitrile at 20℃; for 3h;	2.3.1 Preparation ofTert-butyl 3-(1H-imidazol-1-yl)propylcarbamate In a 50mL round bottom flask Di-tert-butyl dicarbonate(10mmol) was dissolved in 5mL of MeCN, and then1-(3-Aminopropyl)imidazole (10mmol) was added in oneportion. A reaction mixture was stirred for 3h at room temperature. The progress of reaction wasmonitored byThin Layer Chromatography (TLC) using alumina-backedsilica gel 60 (F254) plates eluting with 50% ethyl acetate:petroleum ether. After completion of the reaction, the reactionmixture evaporated under reduced pressure and a crudeproduct was further purified by chromatography over silicagel using ethyl acetate: petroleum ether (3:5, v/v) as eluent.Yield: 99.0%; 1H NMR (500MHz, CDCl3) (ppm): 1.44(s, 9H, -CH3), 1.96 - 2.03 (m, 2H, -CH2), 3.14 (t, J = 5Hz,2H, -CH2), 4.12 (t, J = 5Hz, 2H, -CH2), 4.80 (s, 1H, -NH2),7.09 (d, J = 10Hz, 1H, -CH), 7.21 (d, J = 10Hz, 1H, -CH),8.26 (s, 1H, -CH); 13C NMR (125MHz, CDCl3) (ppm):28.4, 29.7, 37.4, 45.6, 79.6, 120.0, 125.2, 136.5, 156.4; MS(APCI): 226 (M + H)+
92%	With triethylamine In dichloromethane at 20℃; for 2h;
79%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; Cooling with ice;	Synthesis of Boc protected 1-(3-Aminopropyl)imidazole 1-(3-aminopropyl)imidazole (API, 2.4 mL, 20 mmol) was dissolved in THF (50mL). To prepare bi-phasic aqueous condition, a NaHCO3 (4.2g, 50mmol) aqueous solution (50 mL) was added to API solution in an ice bath. A solution of the Boc anhydride (5.6 g, 26 mmol) in 25 mL of THF was added dropwise under vigorous magnetic stirring. After stirring the mixture for 3 h at room temperature, the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate, and washed with water. The organic phase was dried over MgSO4 and concentrated (yield : 79%). 1H NMR (300 MHz, CDCl3, 25°C, TMS): δ (ppm) = 7.5 (s, 1H), 7.0 (s, 1H), 6.9 (s, 1H), 4.8 (s, 1H), 4.0 (t, 2H), 3.1 (q, 2H), 1.9 (quin, 2H), 1.4 (s, 9H).

73%	With sodium hydroxide In tetrahydrofuran at 0℃;	2.3. Synthesis of 1,3-bis-(3-aminopropyl)-1H-imidazol-3-ium chloride(BAPIC) di-tert-butyldicarbonate (4.36 g, 50 mmol) was dissolved in 50 ml THF and cooledto 0 °C. 3-Aminopropylimidazole (2.30 g, 46 mmol) was dissolved in20 ml of 1 M NaOH solution and added slowly, and the solution wasstirred overnight. The solvent was evaporated and the oily productwas dissolved in ethyl acetate and washed with water three times.The organic phase was dried over magnesium sulfate and the solventwas removed, resulting in a viscous oil, which was dried under vacuumovernight (3.02 g, 73%). 1HNMR (400MHz, CDCl3) δ (ppm) 7.37 (s, 1H),6.92 (s, 1H), 6.83 (s, 1H), 5.45 (bs, NH), 3.99 (t, J = 6.8, 2H), 3.00 (m,2H), 1.83 (quin, J = 6.8 Hz, 2H), 1.34 (s, 9 H). 13C NMR (100 MHz,CDCl3, δ, ppm): 156, 136, 129, 118, 79, 44, 37, 31, 28.
	With sodium hydroxide In methanol; water at 20℃; for 4h;	102.A Step A. To 3-(1H-imidazol-1-yl)propylamine (20 mL, 167.6 mmol) dissolved in water (200 mL) and MeOH (200 mL) is added 50% NaOH (aq) until pH 9.5. Di-tert- butyldicarbonate (41 g, 187.9 mmot) is added while stirring at room temperature for 4 hrs and while maintaining the pH at 9.5 with 50% NaOH. The mixture is concentrated in vacuo to remove most MeOH, then is extracted with CH2CI2- The organic phase is dried over anhydrous MgSO4, is filtered and is concentrated in vacuo to give the title compound.
	In tetrahydrofuran at 0 - 20℃; for 0.408333h;
	With sodium hydrogencarbonate at 20℃; for 4h;

Reference： [1]Pore, Dattaprasad M.; Sonawane, Suraj A. [Catalysis Letters, 2022]
[2]Shin, Ju Yeon; Lee, Bang Sook; Jung, Yeongri; Kim, Sung Jin; Lee, Sang-Gi [Chemical Communications, 2007, # 48, p. 5238 - 5240]
[3]Cho, Hong-Jun; Lee, Sang-Myung; Jung, Sungwon; Lee, Tae-Kyung; Yoon, Hyo-Jin; Lee, Yoon-Sik [Tetrahedron Letters, 2011, vol. 52, # 13, p. 1459 - 1461]
[4]Weiss, Ester; Gertopski, Diana; Gupta, Maneesh Kumar; Abu-Reziq, Raed [Reactive and functional polymers, 2015, vol. 96, p. 32 - 38]
[5]Current Patent Assignee: MERCK & CO INC - WO2007/84498, 2007, A1 Location in patent: Page/Page column 208
[6]Location in patent: experimental part Li, Pei; Zhao, Qichao; Anderson, Jared L.; Varanasi, Sasidhar; Coleman, Maria R. [Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 18, p. 4036 - 4046]
[7]Matharu, Avtar S.; Ahmed, Suleiman; Almonthery, Badriya; Macquarrie, Duncan J.; Lee, Yoon-Sik; Kim, Yohan [ChemSusChem, 2018, vol. 11, # 4, p. 716 - 725]

32
[ 5036-48-6 ]
[ 98434-06-1 ]
SKL-2001 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 18h;	To a solution of S-furan-l-yl-isoxazole-S-carboxylic acid(7 retag) and3-imidazol-l-yl-propylamine(0.005 mL) in DMF were added HOBt(8 retag), EDC(9 mg) and TEA(OOl 4 mL). The resulting solution was stirred at a room temperature for 18 hours, and then concentrated under reduced pressure. The resulting concentrate was purified with preparative HPLC to give 4 mg of S-furan-l-yl-isoxazole-S-carboxylic acid (3-imidazol-l-yl-propyl)-amide (yield: 35 %).[182] lH-NMR(acetone-d , 200MHz), ppm(delta): 8.16(bs, IH), 7.86~7.84(m, IH),7.65~7.61(m, IH), 7.19-7.12(m, 2H), 6.97-6.8^m, 2H), 6.78~6.71(m, IH), 4.18(t, 2H), 3.48(q, 2H), 2.24-2.07 (m, 2H) Exact Mass (calc): 286.11 LC-MS ESI+) m/e (M+ 1)+ : 287
35%	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 18h;	To a solution of <strong>[98434-06-1]5-furan-2-yl-isoxazole-3-carboxylic acid</strong> (7 mg) and 3-imidazol-1-yl-propyl amine (0.005 mL) in DMF was added 8 mg of HOBt, 9 mg of EDC and 0.014 mL of TEA. After stirring at room temperature for 18 hrs, the reaction solution was concentrated in vacuo. The obtained concentrate was purified by preparative HPLC to afford 4 mg of <strong>[98434-06-1]5-furan-2-yl-isoxazole-3-carboxylic acid</strong> (3-imidazol-1-yl-propyl)-amide (Yield: 35%). 1H-NMR (acetone-d6, 200 MHz), ppm(delta): 8.16 (bs, 1H), 7.86~7.84 (m, 1H), 7.65~7.61 (m, 1H), 7.19~7.12 (m, 2H), 6.97~6.89 (m, 2H), 6.78~6.71 (m, 1H), 4.18 (t, 2H), 3.48 (q, 2H), 2.24~2.07 (m, 2H) Exact Mass (calc.): 286.11 LC-MS (ESI+) m/e (M+1)+: 287.
35%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 18h;	4) Step 4: Preparation of <strong>[98434-06-1]5-furan-2-yl-isoxazole-3-carboxylic acid</strong> (3-imidazol-l-yl- propyl)-amide (Derivative (I))To a solution of <strong>[98434-06-1]5-furan-2-yl-isoxazole-3-carboxylic acid</strong>(7 mg) and 3-imidazol-l-yl- propyl amine(0.005mL) in DMF was added 8mg of HOBt, 9mg of EDC and 0.014mL of TEA.After stirring at room temperature for 18 hrs, the reaction solution was concentrated in vacuo. The obtained concentrate was purified by preparative HPLC to afford 4 mg of 5-furan-2-yl- <n="37"/>isoxazole-3-carboxylic acid (3-imidazol-l-yl-propyl)-amide (Yield: 35 %). lH-NMR(acetone-d6, 200MHz), ppm(delta): 8.16(bs, IH), 7.86~7.84(m, IH), 7.65~7.61(m, IH), 7.19~7.12(m, 2H), 6.97~6.89(m, 2H), 6.78~6.71(m, IH), 4.18(t, 2H), 3.48(q, 2H), 2.24~2.07(m, 2H) Exact Mass (calc): 286.11 LC-MS (ESI+) m/e (M+l)+ : 287

Reference： [1]Patent: WO2009/5269,2009,A2 .Location in patent: Page/Page column 19
[2]Patent: US2009/131336,2009,A1 .Location in patent: Page/Page column 12
[3]Patent: WO2007/78113,2007,A1 .Location in patent: Page/Page column 35; 36

33
[ 5036-48-6 ]
[ 81-30-1 ]
[ 1025483-96-8 ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: 3-(1H-imidazol-1-yl)propan-1-amine; 1,4,5,8-naphthalenetetracarboxylic dianhydride In ISOPROPYLAMIDE at 125℃; for 18h; Stage #2: With thionyl chloride at 60℃; for 1h;	20 N-[3-(imidazol-l-yl)propyl]-iV'-[8-((2β-dihydrothieno[3,4-b][l,4]dioxin-3- yl)methoxy)-3,6-dioxaoctyI]-l,4,5,8-naphthaIenetetracarboxydiimide (EDOT-ND- Im, 18). A mixture of 11 (804.6 mg, 3 mmol) and l-(3-aminopropyl)imidazole (125.2 mg, 1 mmol) in dimethylacetate (30 mL) was heated at 125°C for 18 hours. Upon cooling to room temperature, the of CHCl3 (100 mL) was added. The precipitate was filtered, and the volatiles removed in vacuum. Water (150 mL) was added and precipitate formed was washed with ethanol and ether. The crude product was heated with SOCl2 (142.8 mg, 1.2 mmol) in DMF at 60 0C for 2 hours. The precipitate formed was collected and washed with ether to afford 17 (251.2 mg, 0.61 mmol, 61%), which was used for the enxt step without further purification. A mixture of 16 (50 mg, 0.17 mmol), 17 (70 mg, 0.17 mmol) and zinc acetate (25.4 mg, 0.12 mmol) was heated in pyridine at 120°C for 15h. After removal of pyridine by vacuum distillation, the reaction mixture was partitioned between CH2Cl2 and Na. The combined organic layer was dried with MgSO4 and subjected to further purification by flash chromatography (dichloromethane/ ethyl acetate = 1/9). The product was obtained as yellow gel (18.5 mg, 0.03 mmol, 17.6% yield). 1H NMR (400 MHz, CDCl3): δ 8.74 (t, 4H, J= 8 Hz), 7.56 (m, IH), 7.02 (m, 2H), 6.32 (d, IH, J= 3.6 Hz), 6.31 (d, 1 H, J= 3.6 Hz)5 4.48 (t, 2H, J = 6 Hz), 4.32- 4.25 (m, IH), 4.23 (dd, IH, J =11.6, 2 Hz), 4.12 (t, 2H, J = 7.6 Hz), 4.05 (dd, IH, J =11.6, 7.2 Hz), 3.87 (dd, IH, J= 10.4, 6 Hz), 3.71 (t, 2H, J= 5.6 Hz), 3.66-3.60 (m, 8 H)5 2.32 (q, 2H, J = 5.6 Hz), 13C NMR (400 MHz, CDCl3): δ 163.1. 163.0, 141.7, 141.6, 137.4, 131.4, 131.2, 129.9, 127.0, 126.9, 126.9, 126.5, 118.8, 100.2, 99.8, 72.8, 71.4, 70.9, 70.7, 70.3, 69.8, 68.0, 66.3, 45.1, 39.8, 38.5, 29.5.
	Stage #1: 3-(1H-imidazol-1-yl)propan-1-amine; 1,4,5,8-naphthalenetetracarboxylic dianhydride In 2,4-dichlorophenoxyacetic acid dimethylamine at 125℃; for 18h; Stage #2: With thionyl chloride In N,N-dimethyl-formamide at 60℃; for 2h;

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2008/57054, 2008, A1 Location in patent: Page/Page column 39; 41
[2]Tansil, Natalia C.; Kantchev, Eric Assen B.; Gao, Zhiqiang; Yu, Hsiao-Hua [Chemical Communications, 2011, vol. 47, # 5, p. 1533 - 1535]

34
[ 7154-73-6 ]
[ 27578-60-5 ]
[ 140-31-8 ]
[ 2038-03-1 ]
[ 25560-00-3 ]
[ 123-00-2 ]
[ 5036-48-6 ]
[ 7663-77-6 ]
[ 34035-03-5 ]
[ 1761-71-3 ]
[ 6864-37-5 ]
[ 2213-43-6 ]
[ 63234-71-9 ]
[ 5906-35-4 ]
[ 59983-39-0 ]
[ 1664-40-0 ]
[ 6530-09-2 ]
[ 108-00-9 ]
[ 109-55-7 ]
[ 51387-90-7 ]
[ 102-83-0 ]
[ 849908-66-3 ]
C₁₅H₁₇ClN₂O [ No CAS ]
[ 849908-70-9 ]
[ 940358-24-7 ]
C₁₆H₁₉ClN₂O [ No CAS ]
C₁₉H₁₉ClN₂O [ No CAS ]
[ 849908-71-0 ]
C₁₇H₂₁ClN₂O₂ [ No CAS ]
[ 849908-67-4 ]
C₁₇H₂₁ClN₂O [ No CAS ]
[ 880815-24-7 ]
C₁₇H₂₂ClN₃O [ No CAS ]
C₁₈H₂₁ClN₂O [ No CAS ]
[ 849908-65-2 ]
[ 932172-19-5 ]
[ 875001-79-9 ]
[ 849908-68-5 ]
[ 849908-69-6 ]
[ 849908-81-2 ]
[ 849908-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	With polymer-bound trimethyl ammonium cyanoborohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 24 - 36h;Combinatorial reaction / High throughput screening (HTS);	All sixty diamines were separated in four groups based on their steric and electronic characteristics, Figures 1-4. Each diamine was measured in the amount of 0.05 g (approximately 0.3 mmol) and pooled together with the others in the group. Obtained diamine mixtures were dissolved in 5 ml of 1,2-dichloroethane and used for the syntheses. Each well of the 96-well filterplates was loaded with 0.2 ml of 1: 10 mixture of acetic acid: DCE, 0.03 ml of the diamine mixture in DCE (group 1, group 2, group 3, or group 4) to assure 0.04 mmol of the diamines per well, and shaken for 5 min at room temperature. Appropriate carbonyl compounds from the master plate (0.1 ml of 1.2 M solution) were added into corresponding wells of the reaction plates followed by the addition of (polystyrylmethyl) trimethylammonium cyanoborohydride, (0.020 g, 0.08 mmol per well). The reaction plates were sealed and placed on a shaker. The reaction was allowed to proceed 24-36 hours at room temperature. At the end, the reaction mixtures were filtered using a filtration manifold, and products were collected into four (one per group) collection plates. Solvents were evaporated in SpeedVac and formed residues were analyzed by mass spectrometry prior to biological screening. Mono and double alkylated products were observed in 1: 0.5 to 1: 2 ratios by mass spectral analysis.

Reference： [1]Patent: WO2005/34857,2005,A2 .Location in patent: Page/Page column 15; 22

35
[ 5036-48-6 ]
[ 452917-27-0 ]
[ 452917-28-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: C-{(1R,2R)-2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropyl}methylamine With 4-Nitrophenyl chloroformate In tetrahydrofuran at 20℃; for 1h; Stage #2: 3-(1H-imidazol-1-yl)propan-1-amine With triethylamine at 35℃; for 2h;	29 [0569] 1-(3-Imidazol-1-yl-propyl)-3-{(1R,2R )-2-[4-(6-trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropylmethyl}-urea (MDL 833306). A solution of C-{(1R,2R )-2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropyl}methylamine (30 mg, 0.081 mmol) and 4-nitrophenyl chloroformate (18 mg, 0.089 mmol ) in anhydrous THF (3 mL ) was stirred at rt under N2 for 1 h. Then Et3N (113 uL, 0.81 mmol ) was added, followed by 3-imidazol-1-yl-propylamine (39 uL, 0.33 mmol). Stirring was continued at 35° C. for 2 h. The reaction mixture was filtered. The filtrate was concentrated, then separated by Prep LC (MeOH/CH2Cl2-5:95, 10:90, 15:85, 20:80, 25:75, 30:70 ) to give the target compound (41 mg, 98%).

Reference： [1]Current Patent Assignee: SANOFI - US2003/229066, 2003, A1 Location in patent: Page 55

36
[ 5036-48-6 ]
[ 2530-83-8 ]
[ 1204776-56-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	In tetrahydrofuran; at 95℃; for 6h;Inert atmosphere;	Example 1 : Synthesis of Compound 1; [68] A Compound 1 represented by Formula 1 was synthesized according to Reaction; Scheme 1 below.[69] <Reaction Scheme 1>[70]^ - « ' ? v ; 1 (J-a»»illi> p«ij»j CMait&XOtt 5 tttrfatovprQp)Jfrin<riho»Hiiota<trLambdarc &fli-alphar > > [71] 162.68 g of tetrahydrofurane, 6.259 g (0.05 mol) of glycidoxypropy- ltrimethoxysilane, and 11.817 g (0.05 mol) of l-(3-aminopropyl)-imidazole were charged into a reactor and were reacted for 6 hours by maintaining the temperature of the reactor at 95 0C under a nitrogen atmosphere with rotating a mechanical stirrer at 300 rpm. After the reaction was completed, a solvent was removed from a resultant for 2 hours by using a rotary evaporator. Then the resultant was dried for 24 hours in a vacuum oven and 7 g (yield 98 %) of Compound 1 represented by Formula 1 was obtained thereby.[72] i H NMR (300 MHz) : delta 0.62~0.68(m, IH), 1.89~1.96(m ,8H), 1.64~1.67(t, 2H), ),2.54~2.56(t, 7H), 2.58~2.61(m, 6H), 3.28~3.31(m, SiOCH3) 3.38~3.40(d, 3H), 3.42~3.44(d,4H), .3.50~3.58(m, 5H), 3.64(s, -NH-), 3.80(s, OH), 4.05-4.10(m, 9H), 6.95(s, 10H), 7.12~7.13(t, HH), 7.65(s, 12H)[73] IR (neat, cm 1) : 3650~3200(vOH), 3300~3200(vNH), 1120~1050(vs,(alkoxy))

Reference： [1]Patent: WO2010/8213,2010,A2 .Location in patent: Page/Page column 10-11

37
[ 5036-48-6 ]
[ 62390-80-1 ]
[ 1070654-72-6 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7069 - 7080

38
[ 5036-48-6 ]
[ 81-84-5 ]
3’-(1’’,8’’-naphthalimid-N’’-yl)-1-propylimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	In N,N-dimethyl-formamide at 90℃; for 24h;	1 Example 1: The 4.95g 1,8- naphthalimide (25mmol)Dissolve with 6.26 g of 1-(3-aminopropyl)imidazole (25 mmol) in 200 mL of N,N-dimethylformamide (DMF).The reaction was stirred at 90 ° C for 24 hours.600 mL of three times of water was added to the reaction solution to crystallize the product, which was allowed to stand overnight at 0 ° C.Filter by suction and wash thoroughly with a large amount of three times of water.The product was sufficiently dried in a vacuum oven to obtain the product naphthalimide imidazole (1) 7.47 g.The yield was 98%.The nuclear magnetic and mass spectral data are shown in Figure 2 and Figure 3.
62.78%	In N,N-dimethyl-formamide Reflux;
40%	With triethylamine In toluene for 72h; Reflux; Molecular sieve; Inert atmosphere;

	In ethyl acetate for 8h; Reflux;
	In ethyl acetate for 5h; Reflux;
	With triethylamine In toluene at 110℃; for 24h; Inert atmosphere; Molecular sieve;
	In N,N-dimethyl-formamide Reflux;
	In ethyl acetate for 5h; Reflux;

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN110105332, 2019, A Location in patent: Paragraph 0027; 0071-0072
[2]Location in patent: experimental part Ozdemir, Saliha; Varlikli, Canan; Oner, Ilker; Ocakoglu, Kasim; Icli, Siddik [Dyes and Pigments, 2010, vol. 86, # 3, p. 206 - 216]
[3]Kilpin, Kelly J.; Clavel, Catherine M.; Edafe, Fabio; Dyson, Paul J. [Organometallics, 2012, vol. 31, # 20, p. 7031 - 7039,9]
[4]Meyer, Andreas; Oehninger, Luciano; Geldmacher, Yvonne; Alborzinia, Hamed; Wölfl, Stefan; Sheldrick, William S.; Ott, Ingo [ChemMedChem, 2014, vol. 9, # 8, p. 1794 - 1800]
[5]Streciwilk, Wojciech; Terenzi, Alessio; Misgeld, Rainer; Frias, Corazon; Jones, Peter G.; Prokop, Aram; Keppler, Bernhard K.; Ott, Ingo [ChemMedChem, 2017, vol. 12, # 3, p. 214 - 225]
[6]Panyam, Pradeep Kumar Reddy; Gandhi, Thirumanavelan [Advanced Synthesis and Catalysis, 2017, vol. 359, # 7, p. 1144 - 1151]
[7]Yurt Lambrecht, Fatma; Ocakoglu, Kasim; Gokhan Colak, Suleyman; Alp Ersoz, Onur; Er, Ozge [Chemical Biology and Drug Design, 2017, vol. 90, # 1, p. 141 - 146]
[8]Streciwilk, Wojciech; Terenzi, Alessio; Lo Nardo, Federico; Prochnow, Pascal; Bandow, Julia Elisabeth; Keppler, Bernhard K.; Ott, Ingo [European Journal of Inorganic Chemistry, 2018, vol. 2018, # 26, p. 3104 - 3112]

39
[ 5036-48-6 ]
[ 134368-28-8 ]
[ 1225209-26-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h;	41.1 Example 41; Synthesis of Compound (I-41); Step (1): Compound 68 → Compound 70; Compound 68 (1.58 g, 4.00 mmol) was dissolved in dichloromethane (30 ml), and then Compound 69 (0.48 ml, 4.00 mmol) and WSCD·HCl (920 mg, 4.80 mmol) were added, followed by stirring at room temperature for 3 hours. After adding water, the organic layer was washed with water, washed with saturated brine, and then dried over magnesium sulfate, subsequently evaporating the solvent under reduced pressure. Diethyl ether was added to the resulting residue, and then filtrated to yield Compound 70 as a colorless powder (1.71 g, 85% yield).Compound 70: 1H-NMR (CDCl3) δ(delta): 2.09 (2H, m), 3.43 (2H, m), 3.80 (3H, s), 3.81 (3H, s), 4.03 (2H, t, J = 6.9 Hz), 5.09 (2H, s), 5.10 (2H, s), 6.28 (1H, t, J = 6.5 Hz), 6.86-6.91 (5H, m), 6.96 (1H, s), 7.06 (1H, s), 7.20 (1H, dd, J = 8.4, 2.0 Hz), 7.31-7.36 (4H, m), 7.45-7.50 (2H, m).

Reference： [1]Current Patent Assignee: SHIONOGI & CO., LTD. - EP2341053, 2011, A1 Location in patent: Page/Page column 83

40
[ 5036-48-6 ]
[ 39824-26-5 ]
[ 1310342-52-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 105℃; for 0.666667h; Inert atmosphere; Microwave irradiation;

Reference： [1]Lukkarila, Julie L.; Da Silva, Sara R.; Ali, Mohsin; Shahani, Vijay M.; Xu, G. Wei; Berman, Judd; Roughton, Andrew; Dhe-Paganon, Sirano; Schimmer, Aaron D.; Gunning, Patrick T. [ACS Medicinal Chemistry Letters, 2011, vol. 2, # 8, p. 577 - 582]

41
[ 5036-48-6 ]
[ 90-02-8 ]
[ 471933-91-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	In methanol for 3h; Reflux;	2-([3-(1H-imidazol-1-yl)propyl]aminopropyliminomethyl)phenol (2) This compound was prepared using a method similar to those previously reported [8,9]. To a solution of Apim (5.43 g, 43.4 mmol) in dry methanol (30 mL) was added salicylaldehyde (5.30 g, 43.4 mmol) with constant stirring. The resulting yellow solution was refluxed for 3 h and then stirred overnight at room temperature. The solvent was then removed under reduced pressure to give a yellow oil, which, on standing for 4 h, yielded yellow crystals of 2. The crystals were recrystallised from toluene, filtered, washed with cold, dry methanol and air-dried (9.5 g, yield 95%). M.p. 83-84°C (lit. 78-80°C). C13H15N3O (229.28): Calc. C, 68.10; H, 6.59; N, 18.33. Found: C, 68.23; H, 6.40; N, 18.24%. 1H NMR (d6-DMSO): δ=13.36 (br s, 1H), 8.54 (s, 1H), 7.64 (s, 1H), 7.43 (d, 1H, J=6.3Hz), 7.34 (t, 1H, J=6.6Hz), 7.21 (s, 1H), 6.91 (m, 3H), 4.05 (t, 2H, J=6.9Hz), 3.54 (t, 2H, J=6.9Hz), 2.10 (p, 2H, J=6.9, 7.2Hz) ppm. 13C NMR (d6-DMSO): δ=166.3, 160.5, 137.2, 132.3, 131.6, 128.5, 119.2, 118.6, 118.5, 116.4, 55.4, 43.8, 31.6ppm. IR (KBr): ν=3434, 3101, 1632, 1576, 1491, 1401, 1276, 1225, 1151, 1079, 887, 808, 760cm-1. LC/TCOF-MS: Calc. for C13H16N3O [M+1]+ 230.3. Found: 230.1%.
92.3%	In toluene Reflux; Inert atmosphere;	Example 8 Synthesis of Compound 8 [0213] [0214] Salicylaldehyde (12.2 g, 100 mmol), 1-(3-aminopropyl)imidazole (12.5 g, 100 mmol), and toluene (50 ml) were added to a 2-neck, 100 ml flask. A significant exotherm was noted when the mixture was swirled at room temperature. A stir bar was added to the flask and a temperature controller, 25 ml Dean-Stark trap, condenser, and bubbler were attached. The mix was stirred and refluxed at 120° C. under an argon blanket. A total of 1.5 ml of H2O was collected after 12.5 hours of reflux. The reaction was allowed to cool, so that a Claisen head could be attached. The mixture was then heated to 110° C. and sparged with argon for 35 minutes. The product became a waxy, light-brown solid upon cooling. A total of 21.3 grams, 92.3% theory, was recovered. The compound was subjected to thermogravimetric analysis (TGA). [0215] The retained weight at 200° C. (TGA ramp rate=10° C./min., air purge) was 98.5% and the decomposition onset was at 250.7° C. The infrared spectrum included prominent absorptions at 3098, 1705, 1630, 1575, 1490, 1393, 1356, 1272, 1224, 1150, 1024, 976, 858, 806, 756 and 659 wavenumbers.
89.4%	In ethanol for 2h; Reflux;	2.1.1 Synthesis of 2-(3-(1H-imidazol-1-yl)propyliminomethyl)phenol (LH) N-(3-Aminopropyl)imidazole (2.05g, 16.4mmol) was added into an ethanol solution (20cm3) of salicylaldehyde (2.00g, 16.4mmol). The mixture was refluxed for 2h and cooled to room temperature. The solvent was removed on a rotatory evaporator and the yellow crystalline solid LH was rinsed thoroughly with petroleum ether. Yield: 3.36g (89.4%). Elemental Anal. Calc. for C13H15N3O: C, 68.10; H, 6.59; N, 18.33. Found: C, 68.34; H, 6.76; N, 18.55%. Main FT-IR absorptions (KBr pellets, cm-1): 3431 (b, w), 3099 (w), 2933 (w), 2902 (w), 1629 (s), 1574 (m), 1492 (m), 1450 (m), 1360 (m), 1273 (s), 764 (s). 1H NMR (500MHz, CDCl3) δ: 13.15 (s, 1H), 8.33 (s, 1H), 7.47 (s, 1H), 7.34 (t, J=7.6Hz, 1H), 7.25 (m, 1H), 7.09 (s, 1H), 6.96 (d, J=8.3Hz, 1H), 6.93 (s, 1H), 6.89 (t, J=7.1Hz, 1H), 4.09 (t, J=6.9Hz, 2H), 3.57 (t, J=6.4Hz, 2H), 2.21 (p, J=6.7Hz, 2H). 1H NMR (500MHz, CH3OD) δ: 8.43 (s, 1H), 7.67 (s, 1H), 7.39-7.27 (m, 4H), 7.17 (s, 1H), 6.98 (s, 1H), 6.94-6.83 (m, 4H), 4.16 (t, J=7.0Hz, 2H), 3.60 (t, J=6.6Hz, 2H), 2.22 (p, J=6.8Hz, 2H). 1H NMR (500MHz, DMSO-d6) δ: 8.53 (s, 1H), 7.64 (s, 1H), 7.45 (dd, J=7.6, 1.4Hz, 1H), 7.34 (t, J=7.6, 1H), 7.21 (s, 1H), 6.95-6.86 (m, 3H), 4.05 (t, J=7.1Hz, 2H), 3.54 (t, J=6.6Hz, 2H), 2.10 (p, J=6.9Hz, 2H). The chemical-shift sequence of hydrogen atoms (from the high field to the low field) is consistent with the alphabetic one (A-H) shown in Fig. 1. UV-Vis in methanol, λmax, nm: 316, 254, 243, 215. Fluorescence emission in methanol, λmax, nm: 445.

69%	With formic acid In methanol at 20℃; for 15h; Inert atmosphere; Schlenk technique;	4.1. Preparation of salicylaldimine ligand HL1 Salicylaldehyde (1.279 g, 12 mmol) was added to a solution of 1-(3-aminopropyl)imidazole (2.002 g, 16 mmol) and formic acid (0.5 ml) inmethanol (15 ml) at room temperature. The resulting reaction mixturewas stirred at room temperature for approximately 15 hrs. The solvent ofthe reaction mixture was removed in vacuo resulting in a yellow oilwhich gradually solidified into a yellow solid.
	In ethanol for 6h; Reflux;

Reference： [1]McGinley, John; McCann, Malachy; Ni, Kaijie; Tallon, Theresa; Kavanagh, Kevin; Devereux, Michael; Ma, Xiaomei; McKee, Vickie [Polyhedron, 2013, vol. 55, p. 169 - 178]
[2]Current Patent Assignee: DESIGNER MOLECULES INC. - US2013/12620, 2013, A1 Location in patent: Paragraph 0214
[3]Qian, Hui-Fen; Dai, Yuan; Geng, Jiao; Wang, Li; Wang, Cheng; Huang, Wei [Polyhedron, 2014, vol. 67, p. 314 - 320]
[4]Tumeli, Ts'epo R.; van Wyk, Juanita L. [Inorganica Chimica Acta, 2021, vol. 527]
[5]Location in patent: experimental part Kalanithi; Rajarajan; Tharmaraj [Journal of Coordination Chemistry, 2011, vol. 64, # 5, p. 842 - 850]

42
[ 5036-48-6 ]
[ 1229016-71-0 ]
[ 1229013-98-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine In acetonitrile at 70 - 80℃; for 4h;	54 Preparation of 2-(4-hydroxyphenylamino)-6-[(3-imidazol-1-yl)propylamino]-3-nitropyridine EXAMPLE 54 Preparation of 2-(4-hydroxyphenylamino)-6-[(3-imidazol-1-yl)propylamino]-3-nitropyridine To 10 ml of acetonitrile were added 477 mg (1.8 mmol) of the 2-(4-hydroxyphenylamino)-6-chloro-3-nitropyridine compound obtained in Preparation Example 1-6, 0.3 ml (2.15 mmol) of triethylamine and 0.26 ml (2.16 mmol) of 1-(3-aminopropyl)imidazole, followed by reaction at a temperature of 70 to 80° for 4 hours. After the reaction was complete, the solvent was distilled under reduced pressure, followed by stirring in 5 ml of methanol for 1 hour at room temperature. The resulting solid was filtered, washed with 5 ml of methanol and then dried under vacuum at about 40° to afford 450 mg (yield: 71%) of the desired compound. Mass (M+): 355.1 1H-NMR (DMSO-d6) (ppm) 1.94(m, 2H), 3.23(m, 2H), 3.96(t, 2H), 6.07(d, 1H), 6.76(d, 2H), 6.89(s, 1H), 7.13(s, 1H), 7.43(d, 2H), 7.59(s, 1H), 8.06(s, 1H), 8.28(t, 1H), 9.40(s, 1H).
71%	With triethylamine In acetonitrile at 70 - 80℃; for 4h;	54 Example 54 Preparation of 2-(4-hydroxyphenylamino)-6-[(3-imidazol-1-yl)propylamino]-3-nitropyridine To 10ml of acetonitrile were added 477mg (1.8mmol) of the 2-(4-hydroxyphenylamino)-6-chloro-3-nitropyridine compound obtained in Preparation Example 1-6, 0.3ml (2.15mmol) of triethylamine and 0.26ml (2.16mmol) of 1-(3-aminopropyl)imidazole, followed by reaction at a temperature of 70 to 80°C for 4 hours. After the reaction was complete, the solvent was distilled under reduced pressure, followed by stirring in 5ml of methanol for 1 hour at room temperature. The resulting solid was filtered, washed with 5ml of methanol and then dried under vacuum at about 40°C to afford 450mg (yield: 71%) of the desired compound. Mass (M+): 355.1 1H-NMR(DMSO-d6) (ppm) 1.94(m, 2H), 3.23(m, 2H), 3.96(t, 2H), 6.07(d, 1H), 6.76(d, 2H), 6.89(s, 1H), 7.13(s, 1H), 7.43(d, 2H), 7.59(s, 1H), 8.06(s, 1H), 8.28(t, 1H), 9.40(s, 1H).

Reference： [1]Current Patent Assignee: DONGWHA PHARM CO.,LTD. - US2011/306606, 2011, A1 Location in patent: Page/Page column 24
[2]Current Patent Assignee: DONGWHA PHARM CO.,LTD. - EP2394993, 2011, A2 Location in patent: Page/Page column 39

43
[ 5036-48-6 ]
[ 1094399-95-7 ]
[ 1229013-99-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine In acetonitrile at 70 - 80℃; for 4h;	55 EXAMPLE 55; Preparation of 2-[4-methylsulfanyl)phenylamino]-6-[(3-imidazol-1-yl)propylamino]-3-nitropyridine; To 10 ml of acetonitrile were added 250 mg (0.84 mmol) of the 2-(4-methylsulfanylphenylamino)-6-chloro-3-nitropyridine compound obtained in Preparation Example 1-7, 0.14 ml (1.01 mmol) of triethylamine and 0.12 ml (1.01 mmol) of 1-(3-aminopropyl)imidazole, followed by reaction at a temperature of 70 to 80° for 4 hours. After the reaction was complete, the solvent was distilled under reduced pressure, followed by column chromatography purification with a 12:1 (v/v) solution of chloroform and methanol as a developing solvent and vacuum drying at about 40° to afford 245 mg (yield: 76%) of the desired compound.Mass (M+): 385.11H-NMR (DMSO-d6) (ppm) 1.99(t, 2H), 2.48(s, 3H), 3.25(m, 2H), 4.01(t, 2H), 6.11(d, 1H), 6.89(s, 1H), 7.16(s, 1H), 7.26(d, 2H), 7.63(m, 3H), 8.09(d, 1H), 8.35(t, 1H), 10.83(s, 1H).
76%	With triethylamine In acetonitrile at 70 - 80℃; for 4h;	55 Example 55 Preparation of 2-[(4-methylsulfanyl)phenylamino]-6-[(3-imidazol-1-yl)propylamino]-3-nitropyridine To 10ml of acetonitrile were added 250mg (0.84mmol) of the 2-(4-methylsulfanyl-phenylamino)-6-chloro-3-nitropyridine compound obtained in Preparation Example 1-7, 0.14ml (1.01mmol) of triethylamine and 0.12ml (1.01mmol) of 1-(3-aminopropyl)imidazole, followed by reaction at a temperature of 70 to 80°C for 4 hours. After the reaction was complete, the solvent was distilled under reduced pressure, followed by column chromatography purification with a 12:1 (v/v) solution of chloroform and methanol as a developing solvent and vacuum drying at about 40°C to afford 245mg (yield: 76%) of the desired compound. Mass (M+): 385.1 1H-NMR(DMSO-d6) (ppm) 1.99(t, 2H), 2.48(s, 3H), 3.25(m, 2H), 4.01(t, 2H), 6.11(d, 1H), 6.89(s, 1H), 7.16(s, 1H), 7.26(d, 2H), 7.63(m, 3H), 8.09(d, 1H), 8.35(t, 1H), 10.83(s, 1H).

Reference： [1]Current Patent Assignee: DONGWHA PHARM CO.,LTD. - US2011/306606, 2011, A1 Location in patent: Page/Page column 24-25
[2]Current Patent Assignee: DONGWHA PHARM CO.,LTD. - EP2394993, 2011, A2 Location in patent: Page/Page column 39

44
[ 5036-48-6 ]
[ 1096857-03-2 ]
[ 1229014-00-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine In acetonitrile at 70 - 80℃; for 20h;	56 Example 56 Preparation of 2-(4-n-butylphenylamino)-6-[(3-imidazol-1-yl)propylamino]-3-nitropyridine To 10ml of acetonitrile were added 280mg (0.92mmol) of the 2-(4-n-butylphenylamino)-6-chloro-3-nitropyridine compound obtained in Preparation Example 1-8, 0.14ml (1.01mmol) of triethylamine and 0.12ml (1.01mmol) of 1-(3-aminopropyl)imidazole, followed by reaction at a temperature of 70 to 80°C for 20 hours. After the reaction was complete, the solvent was distilled under reduced pressure, followed by column chromatography purification with a 15:1 (v/v) solution of chloroform and methanol as a developing solvent and vacuum drying at about 40°C to afford 245mg (yield: 76%) of the desired compound. Mass (M+): 395.0 1H-NMR(DMSO-d6) (ppm) 0.90(t, 3H), 1.31(m, 2H), 1.54(m, 2H), 1.99(m, 2H), 2.50(m, 2H), 3.27(m, 2H), 3.99(t, 2H), 6.11(d, 1H), 6.88(s, 1H), 7.17(m, 3H), 7.60(m, 3H), 8.09(d, 1H), 8.34(t, 1H), 10.84(s,1H).
51%	With triethylamine In acetonitrile at 70 - 80℃; for 4h;	56 EXAMPLE 56; Preparation of 2-(4-n-butylphenylamino)-6-[(3-imidazol-1-yl)propylamino]-3-nitropyridine; To 10 ml of acetonitrile were added 280 mg (0.92 mmol) of the 2-(4-n-butylphenylamino)-6-chloro-3-nitropyridine compound obtained in Preparation Example 1-8, 0.14 ml (1.01 mmol) of triethylamine and 0.12 ml (1.01 mmol) of 1-(3-aminopropyl)imidazole, followed by reaction at a temperature of 70 to 80° for 20 hours. After the reaction was complete, the solvent was distilled under reduced pressure, followed by column chromatography purification with a 15:1 (v/v) solution of chloroform and methanol as a developing solvent and vacuum drying at about 40° to afford 245 mg (yield: 76%) of the desired compound.Mass (M+): 395.01H-NMR (DMSO-d6) (ppm) 0.90(t, 3H), 1.31(m, 2H), 1.54(m, 2H), 1.99(m, 2H), 2.50(m, 2H), 3.27(m, 2H), 3.99(t, 2H), 6.11(d, 1H), 6.88(s, 1H), 7.17(m, 3H), 7.60(m, 3H), 8.09(d, 1H), 8.34(t, 1H), 10.84(s, 1H).

Reference： [1]Current Patent Assignee: DONGWHA PHARM CO.,LTD. - EP2394993, 2011, A2 Location in patent: Page/Page column 39
[2]Current Patent Assignee: DONGWHA PHARM CO.,LTD. - US2011/306606, 2011, A1 Location in patent: Page/Page column 25

45
[ 5036-48-6 ]
[ 10111-08-7 ]
[ 1356408-85-9 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; for 1h;Reflux;	General procedure: Neat secondary aromatic or aliphatic amine (5.0 mmol) was introduced at rt to a solution of imidazole-2-carboxaldehyde (1) (0.48 g, 5.0 mmol) in MeOH (100 mL) and the reaction was stirred at reflux for 1 h. After that time, solvent was evaporated under reduced pressure affording crude imines 2 that were used directly in the next step. The crude imine (5.0 mmol) was dissolved in dry toluene (50 mL) and diethyl phosphite (0.65 mL, 5.0 mmol) or ethyl phenylphosphinate (0.75 mL, 5.0 mmol) was added. The mixture was heated to reflux for 2 h and then concentrated under reduced pressure affording crude esters 3 as thick oils or semi-solids. The phosphinate esters 3c,d were recrystallized from a mixture of toluene/hexane. The phosphonate esters 3a,b were characterized as oxalate salts. The oxalates were obtained in the following way; the crude ester (1.0 equiv) was dissolved in acetone (10 mL) and oxalic acid (COOH)2·2H2O (2.0 equiv) in acetone (10 mL) was added and the mixture was refrigerated. The separated precipitate was filtered, washed with cold acetone (10 mL) and dried on air.

Reference： [1]Tetrahedron,2012,vol. 68,p. 1223 - 1229
[2]Journal of Materials Chemistry B,2017,vol. 5,p. 6869 - 6881

46
[ 5036-48-6 ]
[ 13292-22-3 ]
[ 1332223-35-4 ]

Yield	Reaction Conditions	Operation in experiment
42%		General procedure: Rifaldehyde (290.0 mg, 0.4 mmol) was dissolved in 30 mL CH2Cl2 and after the addition of catalyst (0.2 mmol ZnCl2 or 0.02 mmol HCl/EtOH) respective mixtures were made with each of the following compounds taken separately: propargylamine, 3-azidopropylamine, 2-azidoethylamine, (1-(2-aminoethyl)piperidine, 1-(2-aminoethyl)pyrrolidine, N,N-dimethylethylenediamine, 1-(3-aminopropyl)-imidazole, 3-morpholinopropyl-amine, 4-aminobenzylpiperidine, 1-(3-aminopropyl)pyrrolidine or 3-(dimethylamino)-1-propylamine, 3-(diethylamino)propyl-amine) (0.41 mmol) in 5 mL of C2H5OH. The mixtures were stirred at 45 C for half an hour and after that a half of the solvent volume was distilled off. To the cooled reaction mixture (room temperature) the reductant NaBH4 (6.8 mg, 0.18 mmol) was added portionwise over 1 min. The reaction mixture was evaporated to dryness, dissolved in 50 mL of ethyl acetate and extracted twice with 50 mL of water and brine. The separated organic layer was evaporated and synthesised derivatives of <strong>[13292-22-3]<strong>[13292-22-3]3-formylrifamycin</strong> SV</strong> (compounds 1-12) were then purified by column chromatography with silica gel (25 cm×1 cm, silica gel 60, 0.040-0.063 mm/230-400 mesh ASTM, Fluka) and ethyl acetate/methanol was applied as eluent (from 100:0 to 15:1).

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 2385 - 2388
[2]European Journal of Medicinal Chemistry,2014,vol. 84,p. 651 - 676

47
[ 5036-48-6 ]
[ 4684-94-0 ]
[ 1271446-00-4 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h;	INTERMEDIATE 49 6-Chloro-N-[3-(lH-imidazol-l-yl)propyl]pyridine-2-carboxamide 6-Chloro-pyridine-2-carboxylic acid (1.00 g, 6.35 mmol) was dissolved in DCM (20 mL) and HOBt (1.03 g, 7.62 mmol), EDC.HCl (1.46 g, 7.62 mmol) and l-(3-aminopropyl)imidazole (0.95 g, 7.62 mmol) were added. The reaction mixture was stirred for 18 h, diluted with DCM (130 mL) washed with sat aq Na2C03 (100 mL), brine (30 mL), water (30 mL), dried (MgS04) and concentrated in vacuo. The residue was triturated with water to give the crude title compound (1.05 g, 63%) as an off-white solid. LCMS (ES+): 266 [MH]+.
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h;	6-Chloro-pyridine-2-carboxylic acid (1.00 g, 6.35 mmol) was dissolved in DCM (20 mL) and HOBt (1.03 g, 7.62 mmol), EDC.HCl (1.46 g, 7.62 mmol) and 1-(3-aminopropyl)imidazole (0.95 g, 7.62 mmol) were added. The reaction mixture was stirred for 18 h, diluted with DCM (130 mL) washed with sat aq Na2CO3 (100 mL), brine (30 mL), water (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was triturated with water to give the crude title compound (1.05 g, 63%) as an off-white solid. LCMS (ES+): 266 [MH]+.

Reference： [1]Patent: WO2012/49277,2012,A1 .Location in patent: Page/Page column 40
[2]Patent: US2013/289020,2013,A1 .Location in patent: Paragraph 0149; 0150

48
[ 5036-48-6 ]
[ 605-65-2 ]
[ 1350462-51-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine In dichloromethane at 0 - 20℃; for 1h;
72%	With triethylamine In methanol at 0 - 20℃; for 48.25h;
50%	With triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	Probe 1 To a solution of dansyl chloride (134 mg, 0.5 mmol) in dichloromethane (10 mL), which was stirred at 0-10 °C under argon atmosphere, 1(3-aminopropyl)imidazole (125 mg, 1.0 mmol) was added dropwise. Triethylamine (202 mg, 2.0 mmol) was then added for neutralization of the generated acid; the reaction mixture was stirred at room temperature for 3 h. After completion of the reaction, the reaction mixture was concentrated and purified by silica gel column chromatography with CH2Cl2: CH3OH (9:1) as eluent (Rf = 0.6) to obtain yellow solid 1 (90 mg, 50%). mp. 72 °C (CH2Cl2-hexane); 1H NMR (400 MHz, DMSO-d6) δ 1.67-1.74 (m, 2H, CH2), 2.69-2.74 (m, 2H, CH2), 2.82 (s, 6H, 2 x CH3), 3.86 (t, J = 6.8 Hz, 2H, CH2), 6.88 (s, 1H, ImHb), 6.97 (s, 1H, ImHc), 7.26 (d, J = 6.8 Hz, 1H, ArH), 7.53 (s, 1H, ImHa), 7.61 (t, J = 8.0 Hz, 2H, 2x ArH), 8.02 (t, J = 6.0 Hz, 1H, SO2NH), 8.07 (d, J = 8.0 Hz, 1H,ArH), 8.28 (d, J = 8.8 Hz, 1H, ArH), 8.46 (d, J = 8.8 Hz, 1H, ArH); 13C NMR (100 MHz, DMSO-d6) δ 31.12 (CH2), 39.80 (CH2), 43.42 (CH2), 45.43 (2 x CH3), 115.55, 119.32, 119.42, 124.01, 128.30, 128.68, 128.81, 129.38, 129.45, 129.90, 136.12, 137.40, 151.83; HR-FAB mass calcd for: C18H23N4O2S (M+H)+: 359.1542; Found: m/z 359.1543.

50%

With triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;

1 A solution of 0.5 mmol (134 mg) of dansyl chloride in 10 mL of dichloromethane was stirred at 0 ° C to 10 ° C under argon atmosphere, and to this solution 1 mmol (125 mg) of [1- (3-aminopropyl) -imidazole] was added dropwise. Subsequently, 2 mmol (200 mg) of triethylamine was added for neutralization and the reaction was carried out at room temperature for 3 hours with stirring. After completion of the reaction, the reaction product was concentrated and purified by column chromatography using a solution of CH2Cl2 and ethanol in an amount of 9: 1 by volume as an eluent (Rf = 0.6) to obtain the compound according to Example 1 of the present invention to give a yellow solid (yield 50%, 90 mg)

Reference： [1]Knighton, Richard C.; Sambrook, Mark R.; Vincent, Jack C.; Smith, Simon A.; Serpell, Christopher J.; Cookson, James; Vickers, Matthew S.; Beer, Paul D. [Chemical Communications, 2013, vol. 49, # 23, p. 2293 - 2295]
[2]Zhang, Qinghua; Yang, Benqun; Zhang, Shiguo; Liu, Shimin; Deng, Youquan [Journal of Materials Chemistry, 2011, vol. 21, # 41, p. 16335 - 16338]
[3]Kumar, Ashwani; Kim, Hong-Seok [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 148, p. 250 - 254]
[4]Current Patent Assignee: KYUNGPOOK NATIONAL UNIVERSITY - KR101521757, 2015, B1 Location in patent: Paragraph 0033-0034

49
[ 5036-48-6 ]
[ 20577-64-4 ]
[ 27258-33-9 ]
C₁₈H₂₃N₅O₃ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

50
[ 5036-48-6 ]
[ 1410097-04-9 ]
[ 27258-33-9 ]
C₂₅H₂₄N₆O₃ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

51
[ 5036-48-6 ]
[ 131-56-6 ]
[ 1334482-81-3 ]

Yield	Reaction Conditions	Operation in experiment
97.7%	In toluene; for 17.5h;Inert atmosphere; Reflux;	Example 17 Synthesis of Compound 17 [0239] [0240] Toluene (50 ml), 1-(3-aminopropyl)imidazole (12.5 g, 100 mmol), and <strong>[131-56-6]2,4-dihydroxybenzophenone</strong> (21.42 g, 100 mmol) were charged into a 2-neck, 100 ml flask. A stir bar was placed in the flask and a temperature controller, 25 ml Dean-Stark trap, condenser, and bubbler were attached. The mix was stirred and refluxed at 120 C. under a nitrogen blanket for 17.5 hours. A total of 1.8 ml of H2O was collected in the trap. A Claisen head was attached to the flask and the solvent was distilled off at 125 C. under a nitrogen sparge. A total of 31.4 grams, 97.7% theory, of a yellow-orange, waxy solid was recovered. A TGA run on this compound indicated a retained weight at 200 C. (ramp rate=10 C./min., air purge) of 99.48% and the decomposition onset at 290.6 C. The infrared spectrum included significant absorptions at 1708, 1584, 1442, 1355, 1223, 1167, 1085, 979, 926, 844, 772, and 703, wavenumbers.

Reference： [1]Patent: US2013/12620,2013,A1 .Location in patent: Paragraph 0240

52
[ 5036-48-6 ]
protopanaxadiol [ No CAS ]
[ 1444554-50-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: protopanaxadiol With ozone In dichloromethane at -78℃; for 0.0833333h; Stage #2: 3-(1H-imidazol-1-yl)propan-1-amine With sodium triacetoxyborohydride In methanol; dichloromethane at -78 - 0℃;	General synthetic procedure for compounds 2-26 General procedure: Into a solution of PPD (1, 200 mg, 0.435 mmol) in CH2Cl2 (15 mL) and cooled to -78 °C, ozone was bubbled (at a flow rate of 2.0 L/min of oxygen containing 5% of ozone) with stirring. The mixture was maintained at -78 °C for 5 min. The reaction was monitored by thin-layer chromatography (TLC). The excess of ozone was eliminated by bubbling nitrogen into the solution. Amine (RNH2) (0.1 mL), NaBH(OAc)3 (368.8 mg, 1.7 mmol), and CH3OH (8 mL) were successively added, and the mixture was allowed to reach 0 °C. After completion of the reaction (TLC monitoring, CH2Cl2/CH3OH, 30:1, v/v, on silica gel plate), water was added,and the product was isolated by extraction with dichloromethane. The organic phase was washed with water, brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum toobtain the desired crude products. The appropriate compounds (2-26) were obtained following purification by silica gel column chromatography with dichloromethane/methanol/triethylamine= 60:1:0.5 (v/v/v).

Reference： [1]Liu, Junhua; Wang, Xu; Liu, Peng; Deng, Rongxin; Lei, Min; Chen, Wantao; Hu, Lihong [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 14, p. 4279 - 4287]

53
[ 5036-48-6 ]
[ 10111-08-7 ]
N-[(E)-1H-imidazol-2-ylmethylidene]-N-[3-(1H-imidazol-1-yl)propyl]amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In methanol; for 3h;Reflux;	To a solution of Apim (2.81 g, 22.5 mmol) in dry methanol (17 mL) was added imidazole-2-carboxaldehyde (2.17 g, 22.5 mmol). The resulting solution was heated to reflux for 3 h and then stirred overnight at room temperature. The solvent was removed under reduced pressure to give a brown oil, which, on standing for 2 months, yielded the orange-brown solid (4) (3.69 g, yield 86%). M.p. 44-46C. C10H13N5·0.5H2O (212.15): Calc. C, 56.56; H, 6.59; N, 33.01. Found: C, 56.08; H, 6.32; N, 32.87%. 1H NMR (d6-DMSO): delta=8.17 (s, 1H), 7.65 (s, 1H), 7.19 (s, 1H), 7.13 (s, 1H), 7.11 (s, 1H), 6.91 (s, 1H), 4.06 (t, 2H, J=6.9Hz), 3.43 (t, 2H, J=6.0Hz), 2.01 (t, 2H, J=6.9Hz) ppm. 13C NMR (d6-DMSO): delta=152.3, 144.4, 137.2, 128.2, 119.4, 56.7, 43.9, 31.7ppm. IR (KBr): nu=3114, 1650, 1513, 1446, 1397, 1232, 1109, 1083, 771cm-1. LC/TCOF-MS: Calc. for C10H14N5 [M+1]+ 204.2. Found: 204.1%.

Reference： [1]Polyhedron,2013,vol. 55,p. 169 - 178

54
[ 5036-48-6 ]
[ 68282-53-1 ]
[Ag(3-(1H-imidazol-1-yl)-N-[(E)-(5-methyl-1H-imidazol-4-yl)methylidene]-1-propanamine)]ClO₄ [ No CAS ]

Reference： [1]Polyhedron,2013,vol. 55,p. 169 - 178

55
[ 5036-48-6 ]
[ 68282-53-1 ]
3-(1H-imidazol-1-yl)-N-[(E)-(5-methyl-1H-imidazol-4-yl)methylidene]-1-propanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In methanol; for 3h;Reflux;	To a solution of Apim (2.81 g, 22.5 mmol) in dry methanol (17 mL) was added <strong>[68282-53-1]4-methyl-5-imidazolecarboxaldehyde</strong> (2.17 g, 22.5 mmol). The resulting light-yellow suspension was heated to reflux for 3 h. The suspension was dissolved completely after 5 min. The solution was then stirred overnight at room temperature. After 0.5 h the solution turned orange in colour. The solvent was removed under reduced pressure to give an orange oil, which, on standing for 3 weeks, yielded the orange solid (5) (3.10 g, yield 76 %). M.p. 113-115C. C11H15N5 (217.27): Calc. C, 60.81; H, 6.96; N, 32.23. Found: C, 60.60; H, 6.72; N, 31.35%. 1H NMR (d6-DMSO): delta=8.23 (s, 1H), 7.64 (s, 1H), 7.61 (s, 1H), 7.18 (s, 1H), 6.91 (s, 1H), 4.04 (t, 2H, J=7.2Hz), 3.42 (t, 2H, J=6.6Hz), 2.32 (s, 3H), 2.03 (p, 2H, J=6.9, 6.6Hz) ppm. 13C NMR (d6-DMSO): delta=137.2, 128.3, 119.3, 57.3, 48.5, 43.9, 32.1ppm. IR (KBr): nu=3113, 1643, 1529, 1452, 1395, 1354, 1233, 1110, 1082, 826, 747cm-1. LC/TCOF-MS: Calc. for C10H14N5 [M+1]+ 218.3. Found 218.1%.

Reference： [1]Polyhedron,2013,vol. 55,p. 169 - 178

56
[ 5036-48-6 ]
[ 367-80-6 ]
Ethyl 4-(3-(1H-imidazol-1-yl)propylamino)-3-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	General procedure: Ethyl-4-fluoro-3-nitrobenzoate, 1 (0.5 g, 2.34 mmol), amine [I:4-(2-Aminoethyl)morpholine; II: N-(3-Aminopropyl)imidazole](2.58 mmol), and N,N-Diisopropylethylamine, DIPEA (0.49 mL,2.78 mmol) were mixed in dichloromethane (10 mL). The reactionmixture was stirred overnight at room temperature. After completionof reaction (as evident from TLC), the reaction mixture waswashed with water (10 mLChi 2) followed by 10% Na2CO3 solution(10 mL). The organic layer was dried over Na2SO4 and concentratedunder reduced pressure to afford 2 as brown oil/yellow solid (80-95%).
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	General procedure: Ethyl-4-fluoro-3-nitrobenzoate, 1 (0.5 g, 2.34 mmol), amine[for 5: N-(3-aminopropyl)imidazole; for 6: aniline] (2.58mmol) and N,N-diisopropylethylamine, DIPEA (0.49 mL,2.78 mmol) were mixed in dichloromethane (10 mL). Thereaction mixture was stirred overnight at room temperature.After completion of reaction (as evident from TLC), thereaction mixture was washed with water (10 mL × 2) followedby 10% Na2CO3 solution (10 mL). The organic layerwas dried over Na2SO4 and concentrated under reducedpressure to afford 2 as yellow solid (80-90%).

Reference： [1]Bioorganic Chemistry,2013,vol. 49,p. 33 - 39
[2]Medicinal Chemistry Research,2017,vol. 26,p. 770 - 778

57
[ 5036-48-6 ]
[ 63082-45-1 ]
C₁₄H₁₆FN₃ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2014,vol. 16,p. 146 - 153

58
[ 5036-48-6 ]
[ 63082-45-1 ]
[ 1333631-34-7 ]

Reference： [1]ACS Combinatorial Science,2014,vol. 16,p. 146 - 153

59
[ 5036-48-6 ]
[ 16209-00-0 ]
C₁₆H₁₇N₅O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In dichloromethane; at 20.0℃; for 20h;	Procedure for synthesis of compound 36. A mixture of 4-(lH-pyrazol-l- yl)benzoic acid (35) (278 mg, 1.48 mmol, 1.00 eq.), 3-(lH-imidazol-l-yl)propan-l-amine (4) (200 mg, 1.60 mmol, 1.08 eq.), TBTU (622 mg, 2.00 mmol, 1.35 eq.), triethylamine (0.28 mL, 2.00 mmol, 1.35 eq.) and DCM (10 mL) was stirred at room temperature for 20 hours, diluted with equal volume of saturated aqueous NaHC03 solution and stirred at room temperature for 2 hours. The resulting mixture was extracted with DCM. The organic phase was dried over sodium sulfate and concentrated at reduced pressure. The obtained residue was purified by column chromatography (silica gel, ethyl acetate/MeOH, 20: 1), then was recrystallized from DCM/hexane giving compound 36 (101 mg, 23%) as a yellow solid.

Reference： [1]Patent: WO2015/100322,2015,A1 .Location in patent: Paragraph 0150

60
[ 5036-48-6 ]
C₁₈H₁₂N₂O₂ [ No CAS ]
C₂₄H₂₁N₅O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: C₁₈H₁₂N₂O₂ With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In tetrahydrofuran; dichloromethane at 20℃; for 0.833333h; Stage #2: 3-(1H-imidazol-1-yl)propan-1-amine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 20℃; for 2h;	1 Procedure for synthesis of compound 30 Procedure for synthesis of compound 30. A mixture of compound 29 (4.97 g, 17.24 mmol, 1.0 eq.), TBTU (7.75 g, 24.15 mmol, 1.4 eq.), DCM (50 mL) and THF (150 mL) was stirred at room temperature for 50 minutes. Then 3-imidazol-l-yl-propylamine (4) (2.38 g, 18.98 mmol, 1.1 eq.) and DIPEA (6 mL, 34.50 mmol, 2.0 eq.) were added. The reaction mixture was stirred at room temperature for 2 hours, diluted with saturated aqueous NaHC03 solution (equivalent volume), stirred at room temperature for 1.5 hours and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated at reduced pressure. The obtained residue was purified by column chromatography (silica gel, ethyl acetate/MeOH/NH4OH, 40:2:1) giving compound 30 (5.78 g, 85%) as a white solid.

Reference： [1]Current Patent Assignee: ONCOTARTIS, INC.; POLINSKY, Alexander; KOROTCHKINA, Lioubov; VUJCIC, Slavoljub; CHERNOVA, Olga - WO2015/100322, 2015, A1 Location in patent: Paragraph 0121

61
[ 5036-48-6 ]
[ 82998-57-0 ]
C₁₄H₁₆IN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 20h;	Procedure for synthesis of compound 62. TBTU (920 mg, 2.86 mmol, 1.5 eq.), triethylamine (0.42 mL, 3.00 mmol, 1.6 eq.) and 3-imidazol-l-yl-propylamine (4) (263 mg, 2.10 mmol, 1.1 eq.) were added to a solution of <strong>[82998-57-0]3-iodo-4-methyl-benzoic acid</strong> (61) (500 mg, 1.91 mmol, 1.0 eq.) in DCM (20 mL) and DMF (3 mL). The reaction mixture was stirred at room temperature for 20 hours, then diluted with a saturated aqueous NaHC03 solution (15 mL), again stirred at room temperature for 1.5 hour and extracted with DCM. The organic phase was dried over sodium sulfate and concentrated at reduced pressure. The obtained residue was purified by column chromatography (silica gel; ethyl acetate/MeOH/Nf^OH, 40:2: 1) giving compound 62 (635 mg, 90%) as a yellowish oil. 1H NMR deltaEta (400 MHz, CDC13): 2.12 (m, 2H), 2.45 (s, 3H), 3.47(q, 2H), 4.05 (t, 2H), 6.25 (brs, 1H), 6.96 (s, 1H), 7.09 (s,lH), 7.27 (d, 1H), 7.52 (s, 1H), 7.60 (dd, 1H), 8.17 (d, 1H). APCI-MS (m/z (intensity)): 370.19 ([M+H]+, 100%).

Reference： [1]Patent: WO2015/100322,2015,A1 .Location in patent: Paragraph 0173

62
[ 5036-48-6 ]
[ 451-69-4 ]
(E)-3-(2-fluorophenyl)-N-[3-(imidazol-1-yl)propyl]-2-propenamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%		General procedure: This compound (1.1 g, 7.0 mmol) and WSC·HCl (2.3 g, 12 mmol) were added to a methylene chloride (80 mL) suspension of <strong>[451-69-4]2-fluorocinnamic acid</strong> (1.7 g, 10 mmol) at 0C, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with water, and an organic layer was then dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvents under a reduced pressure was purified with silica gel column chromatography (NH, n-hexane : ethyl acetate = 1:1), to give the captioned compound (0.7 g, 33%).

Reference： [1]Patent: EP2940003,2015,A1 .Location in patent: Paragraph 0060; 0082

63
[ 5036-48-6 ]
3-chloro-2-phenylquinoxaline-6-carbonyl chloride [ No CAS ]
3-chloro-N-[3-(1H-imidazol-1-yl)propyl]-2-phenylquinoxaline-6-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine In tetrahydrofuran at 20℃; for 1h;	2.9 3-Chloro-N- [3-(1H-imidazol-1-yl)propyl] -2-phenyiquinoxaline- 6-carboxamide Crude 3-chloro-2-phenylquinoxaline-6-carbonyl chloride (5.18 g, 85.4 mmol) was dissolved in THF (200 mL), then TEA (7.15 mL, 51.3 mmol) and 3-(lH-imidazol-l-yl)propan-l -amine (2.45 mL, 20.5 mmol) were added. The mixture was stirred at rt for 1 h. The reaction was quenched by the addition of saturated aqueous solution of NaHC03 and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSC^ and concentrated in vacuo. The resulting solid was washed with isopropyl ether/hexane (1: 1, 100 mL) to give 3-chloro-N-(3-(lH-imidazol-l-yl)propyl)-2- phenylquinoxaline-6-carboxamide (5.17 g, 77%) as a light brown solid. XH NMR (300 MHz, DMSO- 6) δ 1.92-2.12 (m, 2 H), 3.19-3.47 (m, 2 H), 4.08 (t, J= 6.9 Hz, 2 H), 6.91 (s, 1 H), 7.13-7.31 (m, 1 H), 7.47-7.63 (m, 3 H), 7.70 (s, 1 H), 7.77-7.99 (m, 2 H), 8.16-8.42 (m, 2 H), 8.48-8.67 (m, 1 H), 8.93 (t, J = 5.4 Hz, 1 H).
2.75 g	With triethylamine In tetrahydrofuran at 20℃; for 0.5h;	11.2 N-(3-(lH-imidazol-l-yl)propyl)-3-chloro-2-phenylquinoxaline-6-carboxamide To a solution of SOCl2 (4.16 mL, 57.0 mmol) and sodium 3-bromo-2-phenylquinoxaline-6- carboxylate (4.0 g, 11.4 mmol) in THF (100 mL) was added 5 drops of DMF at rt. The mixture was stirred at 40 °C overnight. The mixture was concentrated in vacuo. The resulting off-white solid was dissolved in THF (200 mL), then TEA (4.76 mL, 34.2 mmol) and N-(3-aminopropyl)imidazole (1.63 mL, 13.7 mmol) were added to the mixture. The mixture was stirred at rt for 30 min. The mixture was quenched with sat. NaHC03 aq. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgS04 and concentrated in vacuo. The resultant solid was washed with hexane/'Pr20= 1/1 (100 mL) and dried in vacuo to give N-(3-(lH-imidazol-l-yl)propyl)-3-chloro-2- phenylquinoxaline-6-carboxamide (2.75 g, 62%) as a light brown solid. LCMS (ESI+): m/z =392.2 (Μ+Η).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2015/161142, 2015, A1 Location in patent: Paragraph 00262
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2015/161142, 2015, A1 Location in patent: Paragraph 00295

64
[ 5036-48-6 ]
5-(N-benzyl-4-chlorophenylsulfonamido)-3-methylbenzofuran-2-carboxylic acid [ No CAS ]
N-(3-(1H-imidazol-1-yl)propyl)-5-(N-benzyl-4-chlorophenylsulfonamido)-3-methylbenzofuran-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.8%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	General Procedure D for synthesis of 8-9(a-c) General procedure: To a solution of acid 7(a-p) (1 equiv) and amine (1.5 equiv) in dichloromethane were added HoBt (1.5 equiv) and EDCI(1.5 equiv). The reaction mixture was stirred at room temperature overnight, then washed with 5% aqueous HCl, 5% aqueous sodium bicarbonate, water, and brine, and dried. Purification by chromatography afforded 8-9(a-c).

Reference： [1]Yang, Ying-Rui; Wei, Jin-Lian; Mo, Xiao-Fei; Yuan, Zhen-Wei; Wang, Jia-Lin; Zhang, Chao; Xie, Yi-Yue; You, Qi-Dong; Sun, Hao-Peng [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 11, p. 2713 - 2718]

65
[ 98-01-1 ]
[ 5036-48-6 ]
N-(furan-2-ylmethyl)-3-(1H-imidazol-1-yl)propan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: furfural; 3-(1H-imidazol-1-yl)propan-1-amine In ethanol at 20℃; for 2.5h; Molecular sieve; Stage #2: With sodium tetrahydroborate In ethanol at 0 - 20℃;	N-(furan-2-ylmethyl)-3-(1H-imidazol-1-yl)propan-1-amine (4c) General procedure: To a solution of aldehyde 1, 2, 3, or 4 (1.21mmol) in absolute ethanol (12mL) was added the appropriate amine a (1-(pyridin-2-yl)methanamine), b (1-(furan-2-yl)methanamine), or c (3-(1H imidazol-1-yl)propan-1-amine) (1.45mmol) and 4 molecular sieves. The solution was stirred at room temperature for 2.5h and filtered to remove molecular sieves. Sodium borohydride (2.90mmol) was then added in small portion to the resulting ethanol solution at 0°C and the mixture allowed to return at room temperature and stirred overnight. Water (15mL) was added and the solution stirred for 15min before to be concentrated under reduced pressure. The aqueous layer was extracted with DCM (5×5mL), and the combined organic phase was washed with brine, dried with MgSO4, filtered, and evaporated to dryness. Purification by flash chromatography (DCM/MeOH/TEA, 98:1:1 to 90:9:1) yielded 1a (370mg, 90%), 2a (318mg, 78%), 1b (320mg, 70%), 2b (347mg, 76%), 3c (400mg, 99%), or 4c (400mg, 97%) according to the aldehyde and primary amine used. 1H NMR (400MHz, CDCl3) δ: 1.92 (p, J=6.9Hz, 2H), 2.59 (t, J=6.7Hz, 2H), 3.75 (s, 2H), 4.04 (t, J=6.9Hz, 2H), 6.15 (dd, J=0.6, 3.2Hz, 1H), 6.32 (dd, J=1.9, 3.2Hz, 1H), 6.89 (t, J=1.3Hz, 1H), 7.05 (s, 1H), 7.37 (dd, J=0.8, 1.8Hz, 1H), 7.45 (s, 1H). APCI-MS for C11H16ON3 [M+H]+: 206.3m/z

Reference： [1]Ouellet, Charles; Maltais, René; Ouellet, Étienne; Barbeau, Xavier; Lagüe, Patrick; Poirier, Donald [European Journal of Medicinal Chemistry, 2016, vol. 119, p. 169 - 182]

66
[ 5036-48-6 ]
[ 23806-24-8 ]
N-(3-(1H-imidazol-1-yl)propyl)-3-methylthiophene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 2h;	General procedure: A solution of compound 4b (0.4 g, 2.25 mmol),compound 3 (0.45 g, 2.47 mmol), HBTU (1.01 g, 2.69 mmol) and Et3N (0.48 mL, 3.37 mmol) in DMF (10 mL) was stirred at room temperature for 2 h.Then, the mixture was diluted with water (100 mL), and extracted with EtOAc (50mL × 3). The combined organic layers were dried over MgSO4, concentrated and purified by silica gel column chromatography (CH2Cl2: MeOH = 100:2) to give compound 7 (0.63 g, 73%) as a yellow solid, mp: 93-96 C.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 765 - 768

67
[ 5036-48-6 ]
[ 57709-61-2 ]
2,9-bis(N-(1-imidazolyl)propylaminocarbonyl)-1,10-phenanthroline [ No CAS ]

Reference： [1]Dalton Transactions,2016,vol. 45,p. 11624 - 11627

68
[ 5036-48-6 ]
[ 39161-84-7 ]
C₁₄H₁₇N₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-mercaptophenylacetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 24h; Stage #2: 3-(1H-imidazol-1-yl)propan-1-amine In tetrahydrofuran for 48h;	Synthesis of C10d and derivatives General procedure: An appropriate substituted benzoic acid side chain (0.0023 mmol) was activated using CDI (0.0023 mmol) in THF for 24 hours at room temperature. 1-(3-aminopropyl)imidazole (0.0023 mm0l) was added dropwise upon stirring for 48 hours. Solvent was removed under reduced vacuum, and extracted with 4x50 ml of DCM, washed with water 3x100 mL and dried with magnesium sulfate. DCM was then removed under vacuum to yield the specific compounds. Synthesis of lead compounds was confirmed via 1H NMR, mass spectrometry.

Reference： [1]Geldenhuys, Werner J.; Caporoso, Joel; Leeper, Thomas C.; Lee, Yoon-Kwang; Lin, Li; Darvesh, Altaf S.; Sadana, Prabodh [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 303 - 308]

69
[ 5036-48-6 ]
[ 23911-25-3 ]
C₂₂H₃₄N₈O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 20℃; for 12h;	In Step 1, ethylenediaminetetraacetic acid (EDTA) dianhydride (10 mmol) was dissolved in 30 mL of dimethylformamide (DMF) and 20 mmol1H-imidazole-1-propanamine (structure A) was dissolved in 30 mL of DMF. The EDTA dicarboxylic acid solution was added dropwise to the 1H-imidazole-1-propanamine solution at room temperature for 12 hours. The reaction product was precipitated by addition of 60 mL of absolute ethanol, which was then washed with acetone and dried under vacuum. The reaction product comprises, for example, an inner salt as shown by structure (B).

Reference： [1]Patent: TW2016/38085,2016,A .Location in patent: Paragraph 0050

70
[ 5036-48-6 ]
[ 201530-41-8 ]
C₂₇H₂₆N₆O₃ [ No CAS ]

Reference： [1]RSC Advances,2017,vol. 7,p. 11158 - 11169

71
[ 5036-48-6 ]
[ 35438-63-2 ]
1-(3-imidazolepropyl)aminomethylperylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 3-(1H-imidazol-1-yl)propan-1-amine; perylene-3-carbaldehyde With triisopropoxytitanium(IV) chloride In dichloromethane at 20℃; for 15h; Inert atmosphere; Stage #2: With sodium triacetoxy borohydride In dichloromethane for 2h; Inert atmosphere;	2.5.1. Probe 1 A mixture of 3-perylenecarboxaldehyde (50 mg, 0.18 mmol), 1-(3-aminopropyl)imidazole (36 mg, 0.29 mmol), and TiCl(OiPr)3 (0.37 mL,0.29 mmol) in CH2Cl2 (8 mL) was stirred at room temperature for15 h under Ar, followed by the addition of NaBH(OAc)3 (61 mg,0.29 mmol). The resulting mixture was further stirred for 2 h. Afterthe reaction was complete, the solvent was removed, and the residue was neutralizedwith NaHCO3 solution and extractedwith ethyl acetate.The organic layer was dried over anhydrous Na2SO4 and was concentratedto dryness. The crude product was purified by silica gel (neutralizedwith 8% triethylamine in hexane) chromatography (elution withHex:DCM:MeOH:NH4OH: 5:4:0.5:0.5, Rf = 0.5) to give 1 as a brownish-orange solid in 86% yield (60 mg). m.p. = 114-115 °C; 1H NMR(400 MHz, CDCl3) δ 1.98 (m, 2H, He), 2.73 (t, J = 5.1 Hz, 2H, Hf), 3.95(t, J = 8.5 Hz, 2H, Hd), 4.95 (bs, 1H, -NH), 6.79 (s, 1H, Hc), 6.95 (s,1H, Hb), 7.42 (s, 1H, Ha), 7.96-8.00 (m, 5H, Py), 8.07 (m, 5H, Py), 8.07-8.17 (m, 5H, Py), 8.28 (d, J = 7.5 Hz, 1H, Py); 13C NMR (100 MHz,CDCl3) δ 30.2, 44.4, 45.4, 50.7, 118.8, 122.8, 124.6, 124.7, 124.8, 125.2,125.4, 126.0, 127.3, 127.5, 127.6, 128.0, 129.1, 129.2, 130.5, 130.6,131.1, 131.2, 137.1; HR Mass C27H23N3 [M + H]+: 389.1892, Found:m/z 389.1895.

Reference： [1]Pandith, Anup; Hazra, Giridhari; Kim, Hong-Seok [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2017, vol. 178, p. 151 - 159]

72
[ 5036-48-6 ]
[ 1458-18-0 ]
methyl 5-((3-(1H-imidazol-1-yl)propyl)amino)-3-amino-6-chloropyrazine-2-carboxylate [ No CAS ]

Reference： [1]MedChemComm,2017,vol. 8,p. 1022 - 1036
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 9313 - 9320

73
[ 5036-48-6 ]
[ 4655-54-3 ]
N-(3-(1H-Imidazol-1-yl)propyl)-2-methyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With dmap; N,N,N',N'-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	1.4 (4) N-(3-(lH-Imidazol-l-yl) propyl)-2-methyl-4, 9-dioxo-4, 9-dihydronaphtho [2, 3-b] furan-3-carboxamide (Compound 1 or GRC4583) [00176] An exemplary synthesis scheme of Compound 1 is provided below: (0392) (0393) [00177] To a stirred solution of 2-Methyl-4, 9-dioxo-4, 9-dihydronaphtho [2, 3-b] furan-3- carboxylic acid (256.2 mg, 1.0 mmol) , DMAP (12.2 mg, 0.1 mmol) and HBTU (455 mg, 1.2 mmol) in DMF (5 mL) was added l-(3-Aminopropyl)imidazole (180 μ, 1.5 mmol) at room temperature. The solvent was removed by vacuo after the reaction mixture was stirred at room temperature for 1 day. Then the crude was washed by H20, extracted with CH2C12 (10 mL x 3), dried over Na2S04, and concentrated in vacuo. The residue was purified by flash column chromatography (MeOH/CH2Cl2, 0/100 to 1/49) to give Compound 1 as a yellow solid (240 mg, 66 % yield). Rf (5 % MeOH/CH2Cl2) 0.28; IR (neat) 3285, 3095, 2923, 2848, 1650, 1582, 1213, 991, 844, 715 cm"1; 1H NMR (400 MHz, CDC13) δ 9.79 (s, 1H), 8.21 (qd, 7 = 4.0, 1.7 Hz, 2H), 7.83 - 7.76 (m, 2H), 7.59 (s, 1H), 7.07 (s, 1H), 7.00 (s, 1H), 4.11 (t, 7 = 7.0 Hz, 2H), 3.46 (dd, 7 = 12.5, 6.2 Hz, 2H), 2.87 (s, 3H), 2.16 (quint, 7 = 6.8 Hz, 2H); 13C NMR (100 MHz, CDC13) δ 183.3, 172.9, 166.5, 161.5, 151.1, 137.2, 134.8, 134.2, 132.7, 131.4, 129.3, 127.8, 126.9, 125.9, 118.9, 115.1, 44.5, 36.2, 30.9, 14.9; HRMS (ESI+, TOF) calculated for C20Hi8N3O4 [M + H]+ 364.1297, found 364.1289.
66%	With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;

Reference： [1]Current Patent Assignee: NATIONAL TAIWAN UNIVERSITY - WO2017/151625, 2017, A1 Location in patent: Paragraph 00176-00177
[2]Lin, Chia-Yi; Wu, Hsin-Yi; Hsu, Yuan-Ling; Cheng, Ting-Jen Rachel; Liu, Jyung-Hurng; Huang, Rou-Jie; Hsiao, Tzu-Hung; Wang, Chia-Jen; Hung, Pei-Fang; Lan, Albert; Pan, Szu-Hua; Chein, Rong-Jie; Wong, Chi-Huey; Yang, Pan-Chyr [Journal of Medicinal Chemistry, 2020, vol. 63, # 6, p. 3172 - 3187]

74
[ 5036-48-6 ]
2-ethyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-3-carboxylic acid [ No CAS ]
N-(3-(1H-Imidazol-1-yl)propyl)-2-ethyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dmap; N,N,N',N'-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	1.7 (7)N-(3-(lH-imidazol-l-yl)propyl)-2-ethyl-4,9-dioxo-4,9-dihydronaphtho[2,3- Z>]furan-3-carboxamide (Compound 11) [00180] To a stirred solution of 2-Ethyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-3- carboxylic acid (92 mg, 0.34 mmol), DMAP (42 mg, 0.34 mmol) and HBTU (142 mg, 0.37 mmol) in DMF (1.7 mL) was added l-(3-Aminopropyl)imidazole (49 μ, 0.41 mmol) at room temperature. The solvent was removed by vacuo after the reaction mixture was stirred at room temperature for 1 day. Then the crude was washed by H20, extracted with CH2C12 (10 mL x 3), dried over Na2S04, and concentrated in vacuo. The residue was purified by flash column chromatography (MeOH/CH2Cl2, 0/100 to 1/19) to give compound 11 as a yellow solid (116 mg, 90 % yield). Rf (5 % MeOH/CH2Cl2) 0.31; 1H NMR (400 MHz, CDC13) δ 9.82 (s, 1H), 8.26 - 8.18 (m, 2H), 7.84 - 7.74 (m, 2H), 7.66 (s, 1H), 7.08 (s, 1H), 7.02 (s, 1H), 4.12 (t, = 7.0 Hz, 2H), 3.46 (dd, / = 12.5, 6.2 Hz, 2H), 3.35 (q, = 7.5 Hz, 2H), 2.24 - 2.10 (m, 2H), 1.36 (t, = 7.5 Hz, 3H); 13C NMR (100 MHz, CDC13) δ 183.5, 173.0, 171.2, 161.5, 151.3, 137.3, 134.8, 134.2, 132.8, 131.6, 129.5, 127.8, 126.9, 118.9, 114.4, 44.6, 36.3, 31.0, 22.1, 12.0; HRMS (MALDI+, TOF) calculated for C2iH20N3O4 [M + H]+ 378.1448, found 378.1457.
90%	With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;

Reference： [1]Current Patent Assignee: NATIONAL TAIWAN UNIVERSITY - WO2017/151625, 2017, A1 Location in patent: Paragraph 00180
[2]Lin, Chia-Yi; Wu, Hsin-Yi; Hsu, Yuan-Ling; Cheng, Ting-Jen Rachel; Liu, Jyung-Hurng; Huang, Rou-Jie; Hsiao, Tzu-Hung; Wang, Chia-Jen; Hung, Pei-Fang; Lan, Albert; Pan, Szu-Hua; Chein, Rong-Jie; Wong, Chi-Huey; Yang, Pan-Chyr [Journal of Medicinal Chemistry, 2020, vol. 63, # 6, p. 3172 - 3187]

75
[ 5036-48-6 ]
2-isopropyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-3-carboxylic acid [ No CAS ]
N-(3-(1H-Imidazol-1-yl)propyl)-2-isopropyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dmap; N,N,N',N'-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	1.8 (5)N-(3-(lH-imidazol-l-yl)propyl)-2-isopropyl-4,9-dioxo-4,9-dihydronaphtho[2,3- Z>]furan-3-carboxamide (Compound 10) [00181] To a stirred solution of 2-Isopropyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-3- carboxylic acid (41.8 mg, 0.15 mmol), DMAP (18 mg, 0.15 mmol) and HBTU (61 mg, 0.16 mmol) in DMF (0.74 mL) was added l-(3-Aminopropyl)imidazole (21 μ, 0.18 mmol) at room temperature. The solvent was removed by vacuo after the reaction mixture was stirred at room temperature for 1 day. Then the crude was washed by H20, extracted with CH2C12 (10 mL x 3), dried over Na2S04, and concentrated in vacuo. The residue was purified by flash column chromatography (MeOH/CH2Cl2, 1/199 to 1/19) to give compound 10 as a yellow solid (52 mg, 90 % yield). Rf (5 % MeOH/CH2Cl2) 0.32; 1H NMR (400 MHz, CDC13) δ 9.83 (s, 1H), 8.20 (td, J = 5.3, 1.8 Hz, 2H), 7.83 - 7.73 (m, 2H), 7.72 (s, 1H), 7.08 (s, 1H), 7.05 (s, 1H), 4.34 - 4.27 (m, 1H), 4.14 (t, J = 7.0 Hz, 2H), 3.46 (dd, J = 12.4, 6.2 Hz, 2H), 2.17 (quint, J = 6.8 Hz, 2H), 1.37 (s, 3H), 1.36 (s, 3H); 13C NMR (100 MHz, CDC13) δ 183.6, 174.1, 172.9, 161.6, 151.3, 134.8, 134.2, 132.8, 131.6, 128.7, 127.7, 126.8, 125.9, 113.5, 44.8, 36.2, 30.9, 27.7, 20.4; HRMS (ESI+, TOF) calculated for C22H22N304 [M + H]+ 392.1610, found 392.1605.
90%	With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;

Reference： [1]Current Patent Assignee: NATIONAL TAIWAN UNIVERSITY - WO2017/151625, 2017, A1 Location in patent: Paragraph 00181
[2]Lin, Chia-Yi; Wu, Hsin-Yi; Hsu, Yuan-Ling; Cheng, Ting-Jen Rachel; Liu, Jyung-Hurng; Huang, Rou-Jie; Hsiao, Tzu-Hung; Wang, Chia-Jen; Hung, Pei-Fang; Lan, Albert; Pan, Szu-Hua; Chein, Rong-Jie; Wong, Chi-Huey; Yang, Pan-Chyr [Journal of Medicinal Chemistry, 2020, vol. 63, # 6, p. 3172 - 3187]

76
[ 5036-48-6 ]
[ 3265-74-5 ]
N-(3-(1H-imidazol-1-yl)propyl)-2-methylbenzofuran-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With dmap; N,N,N',N'-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate In N,N-dimethyl-formamide at 0℃;	1.15 (15) N-(3-(lH-imidazol-l-yl)propyl)-2-methylbenzofuran-3-carboxamide (Compound 44) [00188] To a stirred solution of 2-methylbenzofuran-3-carboxylic acid (25 mg, 0.14 mmol), DMAP (25.7 mg, 0.21 mmol) and HBTU (80 mg, 0.21 mmol) in DMF (0.7 mL) was added l-(3-Aminopropyl)imidazole (19 μ, 0.16 mmol) at 0 °C. The solvent was removed by vacuo after the reaction mixture was stirred at room temperature for 1 day. The residue was purified by flash column chromatography (MeOH/CH2Cl2, 0/100 to 1/9) to give compound 44 as a colorless oil (37 mg, 95 % yield). Rf (5 % MeOH/CH2Cl2) 0.29; 1H NMR (400 MHz, CDCI3) δ 7.58 - 7.48 (m, 2H), 7.48 - 7.41 (m, 1H), 7.32 - 7.25 (m, 2H), 7.05 (s, 1H), 6.97 (s, 1H), 5.97 (s, 1H), 4.07 (t, = 7.0 Hz, 2H), 3.51 (dd, / = 13.1, 6.7 Hz, 2H), 2.71 (s, 3H), 2.15 (quint, = 6.9 Hz, 2H); HRMS (ESI+, TOF) calculated for Ci6Hi8N302 [M + H]+ 284.1399, found 284.1392.
95%	With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;

Reference： [1]Current Patent Assignee: NATIONAL TAIWAN UNIVERSITY - WO2017/151625, 2017, A1 Location in patent: Paragraph 00187
[2]Lin, Chia-Yi; Wu, Hsin-Yi; Hsu, Yuan-Ling; Cheng, Ting-Jen Rachel; Liu, Jyung-Hurng; Huang, Rou-Jie; Hsiao, Tzu-Hung; Wang, Chia-Jen; Hung, Pei-Fang; Lan, Albert; Pan, Szu-Hua; Chein, Rong-Jie; Wong, Chi-Huey; Yang, Pan-Chyr [Journal of Medicinal Chemistry, 2020, vol. 63, # 6, p. 3172 - 3187]

77
[ 5036-48-6 ]
3-methyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-2-carboxylic acid [ No CAS ]
N-(3-(1H-imidazol-1-yl)propyl)-3-methyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 3-methyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 3-(1H-imidazol-1-yl)propan-1-amine In N,N-dimethyl-formamide at 20℃; for 12h;	1.17 N-(3-(lH-imidazol-l-yl)propyl)-3-methyl-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-2- carboxamide (RJ-LC-07-49) [00201] To a dry and N2-flushed lOmL Schlenk flask equipped with stir bar and septum was added SM (11 mg, 1 eq.) and CDI (11.3mg, 1.05 eq.) in dry DMF (0.05 M, 0.8 mL) and stirred at room temperature for 30 min. After added N-(3-aminopropyl)imidazole (7.7 μ, 1.5eq), the reaction mixture was stirred at room temperature for 12 h. After completion of the reaction, the DMF was removed in vacuo and the crude solid was washed with H20 and Et20 separately to remove impurities yield a yellow solid (14 mg, 86%). Rf (20% MeOH/CHCl3) 0.52. 1H NMR (600 MHz, CDC13) δ 8.16-8.21 (m, 2H), 7.74-7.80 (m, 2H), 7.56 (s, 1H), 7.04-7.10 (m, 2H), 6.98 (s, 1H), 4.07 (t, J = 6.9 Hz, 2H), 3.47-3.51 (q, 6.4 Hz, 2H), 2.75 (s, 3H), 2.13-2.19 (quintet, J= 6.8 Hz, 2H) ; 13C NMR (150 MHz, CDC13) δ 181.1, 174.0, 158.7, 150.8, 146.2, 137.3, 134.4, 134.0, 133.5, 132.2, 129.8, 129.7, 127.5, 127.1, 126.8, 118.7, 118.7, 44.6, 36.5, 31.2, 9.75.

Reference： [1]Current Patent Assignee: NATIONAL TAIWAN UNIVERSITY - WO2017/151625, 2017, A1 Location in patent: Paragraph 00201

78
[ 5036-48-6 ]
[ 5089-70-3 ]
N-(3-(1H-imidazol-1-yl)propyl)-3-(triethoxysilyl)propane-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 24h;	1 3 g (24.0 mmol) of 1- (3-aminopropyl) imidazole was dissolved in 10 ml of acetonitrile, and 9.29 g (71.9 mmol) of diisopropylethylamine was added thereto.At 60 ° C (3-chloropropyl) triethoxysilane5.77 g (24.0 mmol)Was dissolved in acetonitrile(2.8 M) was added dropwise over 12 hours The reaction was carried out with stirring for 12 hours.The obtained reaction product was analyzed by gas chromatography. As a result,N- (3- (1H-imidazol-1-yl) propyl) -3- (triethoxysilyl) -N- (2- (triethoxysilyl) ethyl) propane-1-amine and intermediate N- (3- (1H-imidazol-1-yl)Propyl) -3- (triethoxysilyl)Propane-1-amine and the raw material1- (3-Aminopropyl) imidazole

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2017/76295, 2017, A Location in patent: Paragraph 0139-0141; 0147

79
[ 5036-48-6 ]
[ 2752-65-0 ]
C₄₄H₅₃N₃O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	General procedure: Gambogic acid (0.20 g, 0.32 mmol) was dissolved in 10 mL of anhydrous CH2Cl2,Product 1a (62 mg, 0.38 mmol) was added,EDCI (0.10 g, 0.53 mmol) and DMAP (22 mg, 0.18 mmol) were added and the reaction was stirred at room temperature for 16-24 hours until the reaction was completed.Concentration, column chromatography [V (petroleum ether): V (ethyl acetate) = 2: 1]An orange solid was obtained, 1,200 mg, 65% yield.

Reference： [1]Patent: CN106565739,2017,A .Location in patent: Paragraph 0018; 0019; 0020; 0055; 0056

80
[ 5036-48-6 ]
[ 124-38-9 ]
C₁₀H₁₅N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With Quinuclidine; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate In toluene at 40℃; Irradiation; regioselective reaction;	General procedure for α-alkylation/lactamization of primary aliphatic amines. General procedure: To a 25 ml oven-dried Schlenk sealing tube containing a magnetic stir bar were added [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 (6.6 mg, 0.006 mmol), quinuclidine (11.1 mg,0.1 mmol), primary alkyl amine (0.3 mmol), acrylate (0.2 mmol) and 0.5 ml oftoluene and tAmOH mixture (1/3, vol/vol). The reaction tube was sealed, frozenby liquid nitrogen for 10 min, and evacuated under vacuum and backfilled withCO2 (balloon) three times through a three-way stopcock. Liquid nitrogen andthe CO2 balloon were then removed. The reaction tube was sealed and allowedto stand at room temperature for 10 min, at which time the plug of the tube wasslowly opened to release the excess CO2 gas. The tube was then resealed and placedapproximately 3 inches away from a Kessil LED illuminator. The reaction mixturewas stirred and irradiated for 24-48 h. The internal temperature was measured tobe approximately 40 °C using an infrared thermometer. The crude mixture wasthen concentrated in vacuo and purified by flash chromatography on silica gelwith a 4g column on a Teledyne ISCO CombiFlash Rf+ Lumen instrument usingthe indicated solvent system.

Reference： [1]Ye, Juntao; Kalvet, Indrek; Schoenebeck, Franziska; Rovis, Tomislav [Nature Chemistry, 2018, vol. 10, # 10, p. 1037 - 1041]

81
[ 5036-48-6 ]
[ 206257-39-8 ]
[ 1356941-10-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 12h; Inert atmosphere;
94%	With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 12h; Inert atmosphere;	7A Example 7A: Synthsis of ethyl 4-((3-(1H-imidazol-1-yl)propyl)amino)-6-bromoquinoline-3-carboxylate (compound 15): Compound 4 (lg, 3.l8mmol) was dissolved in 1,4-dioxane (5mL) under N2 atmosphere. To the reaction mixture dry DIPEA (l.l lmL, 6.36mmol) and 3- (l/7-imidazol-1-yl)propan-l -amine (0.57mL, 4.77mmol) were added respectively. The reaction mixture was allowed to stir for 12 hours at room temperature. Then it was poured into 50mL water. The solid obtained was filtered and dried to give compound 15 (l.2g, 94%) as a white solid. 1H NMR (600 MHz, CDCl3) d ppm 9.29 (t, / = 4.8 Hz, -NH), 9.10 (s, 1H), 8.23 (d, / = 2.4 Hz, 1H), 7.82 (d, / = 9 Hz, 1H), 7.73 (dd, J = 9, 1.8 Hz, 1H), 7.46 (s, 1H), 7.06 (s, 1H), 6.90 (s, 1H), 4.41 (q, / = 7.2 Hz, 2H), 4.15 (t, / = 7.2 Hz, 2H), 3.78-3.75 (m, 2H), 2.28-2.23 (m, 2H), 1.43 (t, / = 7.2 Hz, 3H). ESI-MS m/z 403.32 (M+H+).
	With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 12h; Inert atmosphere;	5.2. Synthesis of ethyl 4-((3-(1H-pyrrol-1-yl)propyl)amino)-6-bromoquinoline-3-carboxylate (5) General procedure: Compound 4 (1 g, 3.18 mmol) was dissolved in 1,4-dioxane (5 mL) under N2 atmosphere. To the reaction mixture dry DIPEA(1.3 mL, 7.98 mmol) and 3-(1H-pyrrol-1-yl)propan-1-amine(0.793 g, 6.39 mmol) were added respectively. The reactionmixture was allowed to stir for 12 h at 60 C. The reaction mixturewas cooled to room temperature and extracted with ethyl acetate.The crude mass obtained was purified by column chromatographyby 50% ethyl acetate in pet ether to give compound 5 (0.25 g, 20%)as a white solid.

Reference： [1]Kundu, Biswajit; Das, Subhendu K.; Paul Chowdhuri, Srijita; Pal, Sourav; Sarkar, Dipayan; Ghosh, Arijit; Mukherjee, Ayan; Bhattacharya, Debomita; Das, Benu Brata; Talukdar, Arindam [Journal of Medicinal Chemistry, 2019, vol. 62, # 7, p. 3428 - 3446]
[2]Current Patent Assignee: INDIAN ASSOCIATION FOR THE CULTIVATION OF SCIENCE; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2019/229765, 2019, A1 Location in patent: Page/Page column 24; 44-45
[3]Kundu, Biswajit; Sarkar, Dipayan; Chowdhuri, Srijita Paul; Pal, Sourav; Das, Subhendu K.; Das, Benu Brata; Talukdar, Arindam [European Journal of Medicinal Chemistry, 2020, vol. 202]

82
[ 5036-48-6 ]
C₅₉H₈₆ClFeN₄O₁₆ [ No CAS ]
C₆₅H₉₅ClFeN₇O₁₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; Cooling with ice;	Mesohemin-MPEG550-N-[3-(1-imidazoyl)propyl]amide (MH-MPEG-N) synthesis. This mesohemin derivative was synthesized in a manner similar to the previously published method.Mesohemin-MPEG550 (550 mg, 0.630 mmol), 1-(3-aminopropyl)imidazole (158 mg, 1.260mmol), and N-(3-dimethylaminopropyl)-N(ethylcarbodiimide hydrochloride (EDC·HCl) (266mg, 1.390 mmol) and DMAP (8 mg, 0.070 mmol) were mixed in 10 mL of DCM in a smallflask while on ice bath. The reaction mixture was brought to room temperature and stirred for24h. After completion of reaction the solution was washed with 0.1 M HCl (3x10 ml), withsaturated NaHCO3 (2x10 ml), and washed with slightly acidic 1M NaBr, and passed throughshort NaBr column. After that mixture was dried with MgSO4 and solvent was removed underreduced pressure yielding 707 mg of mesohemin-(MPEG550)2 (87 % yield). The finalcompound was analyzed by ESI-MS and UV-Vis. λmax: 401, 496, 518, 567 and 621 nm. m/z[M+Na]+: 981.6 - 1605.4 with interval of 44 (M+).

Reference： [1]Fu, Liye; Simakova, Antonina; Park, Sangwoo; Wang, Yi; Fantin, Marco; Matyjaszewski, Krzysztof [Molecules, 2019, vol. 24, # 21]

83
[ 5036-48-6 ]
[ 5428-43-3 ]
C₄₈H₄₅N₆O₃⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In chloroform at 145℃; for 16h;	1 To a high pressure vessel was added 1-(3-aminopropyl)imidazole (0.200 g, 1.60 mmol), triethylamine (0.647 g, 6.39 mmol), 2-chloro-N,N-diphenylacetamide (1.18 g, 4.49 mmol) and chloroform (5 ml_). The vessel was stoppered and stirred at 145°C on an oil bath for 16 hours. The reaction mixture was washed with pH 1 HCI (15 ml_), then water (4x 150 ml_). The organic layer was dried over magnesium sulfate and concentrated in vacuo to give an orange/brown solid (7) (0.883 g, 70 %).
70%	With triethylamine In chloroform at 145℃; for 16h;	1 [MAIL-Ph⁺][NTf₂^·] To a high pressure vessel was added 1-(3-aminopropyl)imidazole (0.200 g, 1.60 mmol), triethylamine (0.647 g, 6.39 mmol), 2-chloro-N,N-diphenylacetamide (1.18 g, 4.49 mmol) and chloroform (5 ml_). The vessel was stoppered and stirred at 145°C on an oil bath for 16 hours. The reaction mixture was washed with pH 1 HCI (15 ml_), then water (4x 150 ml_). The organic layer was dried over magnesium sulfate and concentrated in vacuo to give an orange/brown solid (7) (0.883 g, 70 %).
70%	With triethylamine In chloroform at 145℃; for 16h;	1 To a high pressure vessel was added 1-(3-aminopropyl)imidazole (0.200 g, 1.60 mmol), triethylamine (0.647 g, 6.39 mmol), 2-chloro-N,N-diphenylacetamide (1.18 g, 4.49 mmol) and chloroform (5 mL). The vessel was stoppered and stirred at 145° C. on an oil bath for 16 hours. The reaction mixture was washed with pH 1 HCl (15 mL), then water (4×150 mL). The organic layer was dried over magnesium sulfate and concentrated in vacuo to give an orange/brown solid (7) (0.883 g, 70%).

Reference： [1]Current Patent Assignee: SEREN TECH - WO2019/239150, 2019, A1 Location in patent: Page/Page column 30-31
[2]Current Patent Assignee: SEREN TECHNOLOGIES - WO2019/239149, 2019, A1 Location in patent: Page/Page column 30; 34
[3]Current Patent Assignee: SEREN TECHNOLOGIES - US2021/285072, 2021, A1 Location in patent: Paragraph 0178; 0188

84
[ 5036-48-6 ]
[ 131747-69-8 ]
3-([(2-fluoropyridin-4-yl)methyl][3-(1H-imidazol-1-yl)propyl]amino}methyl)-7,8-dimethyl-4H-chromen-4-one [ No CAS ]

Reference： [1]Patent: WO2019/238786,2019,A1

85
[ 5036-48-6 ]
[ 131747-69-8 ]
[(2-fluoropyridin-4-yl)methyl][3-(1H-imidazol-1-yl)propyl]amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%		A suspension of 3-(1 Aimidazol-1-yl)propan-1 -amine (200 mg, 1.599 mmol, 1.00 eq), 2-fluoro- pyridine-4-carboxaldehyde (200 mg, 1.599 mmol, 1.00 eq) and anhydrous MgS04 (385 mg, 3.197 mmol, 2 eq) in DCE (8 mL) was stirred at rt for 72 h. Then, the mixture was cooled down to 0C and sodium triacetoxyborohydride (474 mg, 2.238 mmol, 1.4 eq.) was added in one por- tion. The reaction was allowed to reach rt over 16 h. The reaction mixture was diluted in water and washed with DCM. Aqueous layer was basified with 5N NaOH and extracted with DCM. The layers were separated. Organic layer was dried, filtered off and concentrated to afford the title compound (200 mg, 0.854 mmol, yield 48%) as a transparent oil. ESI-MS: 235 [M+H]+ 1H NMR (300 MHz, DMSO-ofe) d 8.17 - 8.13 (m, 1H), 7.60 - 7.57 (m, 1H), 7.34 - 7.28 (m, 1H), 7.14 (t, J= 1.3 Hz, 1H), 7.12 (bs, 1H), 6.87 - 6.86 (m, 1H), 4.02 (t, 7= 7.0 Hz, 2H), 3.75 (s, 2H), 2.41 (t, J= 6.7 Hz, 2H), 1.90 - 1.80 (m, 2H).

Reference： [1]Patent: WO2019/238786,2019,A1 .Location in patent: Page/Page column 62

86
[ 5036-48-6 ]
[ 3121-61-7 ]
C₁₂H₂₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; tetrabutylammoniun azide In acetonitrile at 25 - 26℃; for 20h; Sealed tube; Irradiation;

Reference： [1]Alder, Catherine M.; Ballantyne, George; Cresswell, Alexander J.; Cunningham, William B.; Edwards, Lee J.; Grayson, Matthew N.; Kinsella, Anna G.; McKay, Blandine S. J.; Mules, Tom; Ryder, Alison S. H.; Turner-Dore, Jacob [Angewandte Chemie - International Edition, 2020, vol. 59, # 35, p. 14986 - 14991][Angew. Chem., 2020, vol. 132, # 35, p. 15096 - 15101,6]

87
[ 5036-48-6 ]
[ 618-88-2 ]
[ 6147-53-1 ]
[ 33513-42-7 ]
[Co(1-(3-aminopropyl)imidazole)(nita)]·DMF [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53.7%	With nitric acid In water at 100℃; for 48h; High pressure;	Synthesis of Co-MOF : A mixture of api (15 mg, 0.06 mmol), nita (10 mg, 0.04 mmol) and Co(CH 3 COO) 2 ·4H 2 O (11 mg, 0.04 mmol), in a mixture of DMF/H 2 O (3:1, v/v , 2 mL) followed by the addition of few drops of dilute nitric acid; were placed in a 5 mL glass vial with screw cap and then placed in a programmable oven at 100 °C for 48 h, and finally cooled to room temperature. The needle- shaped purple coloured crystals fit for single crystal X-ray analysis were collected. Yield, 10.1 mg (53.7%; based on nita). Anal. Clad., for C 14 H 14 CoN 4 O 6 .DMF: C, 43.28%; H, 4.07%; N, 14.66%; Found: C, 42.77%; H, 3.60%; N, 14.44%. FT-IR (selected peaks, cm -1 ): 1673.23 (C = O); 1625.29, 1567.93 (COO); 3305.33, 3121.45 (NH 2 ).

Reference： [1]Kataria, Ramesh; Kirandeep; Kumar, Girijesh; Mehta, Surinder Kumar; Sahoo, Subhash Chandra; Sharma, Aashima; Sushila [Journal of Molecular Structure, 2021, vol. 1226]

88
[ 5036-48-6 ]
zinc(II) nitrate hexahydrate [ No CAS ]
[ 618-88-2 ]
[ 33513-42-7 ]
[Zn₂(1-(3-aminopropyl)imidazole)₂(nita)₂]·DMF [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.2%	With nitric acid In water at 100℃; for 48h; High pressure;	Synthesis of Co-MOF : General procedure: A mixture of api (15 mg, 0.06 mmol), nita (10 mg, 0.04 mmol) and Co(CH 3 COO) 2 ·4H 2 O (11 mg, 0.04 mmol), in a mixture of DMF/H 2 O (3:1, v/v , 2 mL) followed by the addition of few drops of dilute nitric acid; were placed in a 5 mL glass vial with screw cap and then placed in a programmable oven at 100 °C for 48 h, and finally cooled to room temperature. The needle- shaped purple coloured crystals fit for single crystal X-ray analysis were collected.

Reference： [1]Kataria, Ramesh; Kirandeep; Kumar, Girijesh; Mehta, Surinder Kumar; Sahoo, Subhash Chandra; Sharma, Aashima; Sushila [Journal of Molecular Structure, 2021, vol. 1226]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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CAS No. :	5036-48-6	MDL No. :	MFCD00009819
Formula :	C₆H₁₁N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KDHWOCLBMVSZPG-UHFFFAOYSA-N
M.W :	125.17	Pubchem ID :	78736
Synonyms :

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3267
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P315	Get immediate medical advice/attention.
P320
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P321
P322
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P342	If experiencing respiratory symptoms:
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
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P370	In case of fire:
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P372	Explosion risk in case of fire.
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P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 5036-48-6 ] {[proInfo.proName]}

Quality Control of [ 5036-48-6 ]

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[ 5036-48-6 ] Synthesis Path-Downstream 1~88

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[ 5036-48-6 ]

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[ 5036-48-6 ]

Imidazoles

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[ CAS No. 5036-48-6 ] {[proInfo.proName]}

Quality Control of [ 5036-48-6 ]

Related Doc. of [ 5036-48-6 ]

Product Details of [ 5036-48-6 ]

Safety of [ 5036-48-6 ]

Application In Synthesis of [ 5036-48-6 ]

[ 5036-48-6 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 5036-48-6 ]

Amines

Related Parent Nucleus of [ 5036-48-6 ]

Imidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 5036-48-6 ]

Related Parent Nucleus of
[ 5036-48-6 ]