Name: Benzo[d]thiazol-2-amine
Brand: Ambeed
SKU: A153771
Rating: 4.1 (143 reviews)

1
[ 136-95-8 ]
[ 1001-26-9 ]
[ 58099-45-9 ]

References: [1]Chemische Berichte,1975,vol. 108,p. 3894 - 3897.

2
[ 136-95-8 ]
[ 403-29-2 ]
[ 7067-87-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With water; bovine serum albumin at 20℃; for 10h; Green chemistry;	General procedure for the synthesis of different imidazo [1,2-a] pyridines (11a-11c) and benzo [d] imidazo [2,1-b] thiazoles derivative (12a-12c) from substituted 2-Br acetophenone and 2-amino pyridine (9) or 2-amino benzothiazole (11) (Table 8). General procedure: 2-Amino pyridine (0.25 mmol) or 2 amino benzothiazoles, substituted 2-Br acetophenone (7a-7c, 0.25 mmol) and BSA (50mg) in water (600µL) was stirred at room temperature. till completion of the reaction as monitored by TLC. After the completion of reaction, the reaction mixture was taken in ethyl acetate (5x10 mL) and water (3x10mL). The combined organic layer was dried over anhydrous Na2SO4 and vacuum evaporated using rotavapor. Further, the crude product was purified using silica gel (60-200 mesh size) using varying conc. of Hexane/EtOAc as a eluting solvent (from 95:05 to 90:10). Purified products (11a-11c and 12a-12c, Table 7) were identified and confirmed by their 1H, 13C NMR spectra and HRMS/MS values.
	In ethanol at 70℃; for 18h;
	With sodium hydrogencarbonate In ethanol at 60℃;

With sodium hydrogencarbonate In ethanol at 80℃;

References: [1]Saima; Lavekar, Aditya G.; Equbal, Danish; Sinha, Arun K. [Synthetic Communications, 2022, vol. 52, # 6, p. 834 - 848].
[2]Buu-Hoi,N.P. et al. [Bulletin de la Societe Chimique de France, 1966, p. 1277 - 1279].
[3]Singh, Davinder; Tali, Javeed Ahmad; Kumar, Gulshan; Shankar, Ravi [New Journal of Chemistry, 2021, vol. 45, # 44, p. 20551 - 20555].
[4]Thunga, Sanjeeva; Singh, Neetika; Anugu, Naveenkumar; Kokatla, Hari Prasad [Journal of Organic Chemistry, 2024].

3
[ 136-95-8 ]
[ 2065-04-5 ]
[ 99582-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	In butanone for 2h; Heating;

References: [1]Mase, Toshiyasu; Arima, Hideki; Tomioka, Kenichi; Yamada, Toshimitsu; Murase, Kiyoshi [Journal of Medicinal Chemistry, 1986, vol. 29, # 3, p. 386 - 394].

4
[ 136-95-8 ]
[ 34635-34-2 ]
[ 78220-94-7 ]

Yield	Reaction Conditions	Operation in experiment
40%	With dicyclohexyl-carbodiimide In 1,4-dioxane; N,N-dimethyl-formamide 1.) 1 h, 0 deg C 2.) 3 h, 20 deg C 3.) 24 h, R_.T_.;

References: [1]El-Naggar, A. M.; El-Salam, A. M. Abd; Gommaa, A. M. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 12, p. 1068 - 1070].

5
[ 136-95-8 ]
[ 105397-92-0 ]
[ 105397-98-6 ]

Yield	Reaction Conditions	Operation in experiment
11%	With 1,1'-carbonyldiimidazole 1.) THF, RT_., 1 h, 2.) THF, RT_., 1 h;

References: [1]Katagi; Aoki; Kashiwagi; Ohata; Kohno; Murata; Inoi [Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 11, p. 4878 - 4888].

6
[ 136-95-8 ]
[ 1123-98-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With pyridine hydrogenfluoride; sodium nitrite 1.) O deg C, 20 min, 2.) 50 deg C, 1 h;
	Multi-step reaction with 2 steps 1: (i) aq. H₃PO₄, NaNO₂, (ii) aq. HBF₄ 2: (heating with KF)
	Multi-step reaction with 2 steps 1: ethanol / 80 °C 2: potassium fluoride / acetonitrile / 80 °C

References: [1]Yoneda; Fukuhara [Tetrahedron, 1996, vol. 52, # 1, p. 23 - 36].
[2]Gruenert,C.; Wiechert,K. [Zeitschrift fur Chemie, 1970, vol. 10, p. 188 - 189].
[3]Ghiazza, Clément; Faber, Teresa; Gómez-Palomino, Alejandro; Cornella, Josep [Nature Chemistry, 2022, vol. 14, # 1, p. 78 - 84].

7
[ 136-95-8 ]
[ 1186-73-8 ]
[ 224313-89-7 ]

References: [1]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 237 - 240.

8
[ 136-95-8 ]
[ 1186-73-8 ]
N3-(benzo<d><1,3>thiazolyl)-2-hydroxy-4-oxo-4H-benzo<4,5>thiazolo<3,2-a>pyrimidinecarboxamide [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 237 - 240.

9
[ 136-95-8 ]
[ 627-18-9 ]
[ 58929-72-9 ]
2-imino-3-(γ-hydroxypropyl)benzothiazoline [ No CAS ]
bis[3-(γ-hydroxypropyl)benzothiazol-2-ylidene]ammonium bromide [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1999,vol. 35,p. 860 - 865.

10
[ 136-95-8 ]
[ 89123-01-3 ]
[ 324025-13-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	Multistep reaction;

References: [1]Millan, David S.; Prager, Rolf H. [Australian Journal of Chemistry, 2000, vol. 53, # 7, p. 615 - 618].

11
[ 136-95-8 ]
[ 1798-83-0 ]
2,4-bis-(4-chlorobenzoyl)-2,3-dihydro-1H-pyrido[2,1-b][1,3]benzothiazole [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 555 - 559.

12
[ 136-95-8 ]
[ 387-45-1 ]
[ 68-11-1 ]
[ 907558-63-8 ]

Yield	Reaction Conditions	Operation in experiment
41%	In toluene Heating;
	at 80 - 100℃; Microwave irradiation; Inert atmosphere;

References: [1]Rawal, Ravindra K.; Tripathi, Rajkamal; Katti; Pannecouque, Christophe; De Clercq, Erik [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 4, p. 1725 - 1731].
[2]Pitta, Eleni; Geronikaki, Athina; Surmava, Sofiko; Eleftheriou, Phaedra; Mehta, Vaibhav P.; Van Der Eycken, Erik V. [Journal of Enzyme Inhibition and Medicinal Chemistry, 2013, vol. 28, # 1, p. 113 - 122].

13
[ 136-95-8 ]
[ 7067-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: butan-2-one / 2 h / Heating 2: 2-methoxy-ethanol / 1 h / Heating

References: [1]Mase, Toshiyasu; Arima, Hideki; Tomioka, Kenichi; Yamada, Toshimitsu; Murase, Kiyoshi [Journal of Medicinal Chemistry, 1986, vol. 29, # 3, p. 386 - 394].

14
[ 136-95-8 ]
[ 25141-58-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In thionyl chloride; ethanol; dichloromethane	R.2 Reference Example 2 Reference Example 2 A solution of α-(2-isopropylphenoxy)acetic acid (13.1 g) in thionyl chloride (30 ml) is refluxed for 30 minutes. The mixture is concentrated under reduce pressure to remove the excess thionyl chloride, and the resultant is dissolved in dichloromethane (50 ml). The mixture is added dropwise into a solution of 2-aminobenzothiazole (9.1 g) and pyridine (7.2 ml) in dichloromethane (100 ml) under ice-cooling. The mixture is stirred at the same temperature for five hours, and then washed with water, dried, and concentrated under reduced pressure. To the residue is added ethanol to give 2-(2-isopropylphenoxymethylcarbonylamino)benzothiazole (16.66 g). Yellow powder; 1 H-NMR (CDCl3) δppm: 1.32 (6H, d, J=7 Hz) 3.43 (1H, sept, J=7 Hz), 4.78 (2H, s), 6.85 (1H, dd, J=1 Hz, J=8 Hz), 7.0-7.55 (5H, m), 7.8-7.9 (2H, m), 9.74 (1H, br).

References: [1]Current Patent Assignee: OTSUKA PHARMACEUTICAL - US6140330, 2000, A.

15
[ 136-95-8 ]
[ 2644-70-4 ]
[ 615-21-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In ethylene glycol	1 2-HYDRAZINOBENZOTHIAZOLE EXAMPLE 1: 2-HYDRAZINOBENZOTHIAZOLE To a slurry of 30 g. (0.2 mole) 2-aminobenzothiazole in 150 ml. ethylene glycol was added 23.7 g. (0.4 mole) 85% hydrazine hydrate and 13.7 g. (0.2 mole) hydrazine monohydrochloride. The mixture was stirred under a nitrogen atmosphere and heated at a temperature of 140°C. for 2 hours. The product crystallized on cooling. After addition of 50 ml. water and stirring, the material was filtered, washed with 100 ml. water in three portions, and dried in vacuo at 60°C.

References: [1]Current Patent Assignee: DOWELANCO - US3937714, 1976, A.

16
[ 136-95-8 ]
[ 17823-69-7 ]
[ 183998-94-9 ]

References: [1]Chemistry of Heterocyclic Compounds,2007,vol. 43,p. 382 - 386.

17
[ 136-95-8 ]
[ 108-86-1 ]
[ 1843-21-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With Pd(tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide)(dibenzylideneacetone); caesium carbonate In isopropyl alcohol at 80℃; for 24h;	General experimental procedure for arylation of amines and phenols General procedure: To a stirred solution of aryl halide (1.2mmol) and [Pd(pp3S4)(dba)] (1mol %) in isopropanol (2.5ml) was added nitrogen/oxygen nucleophile (1mmol) followed by Cs2CO3 (2mol %) in the atmosphere of air. The mixture was heated to 80°C and the progress of the reaction was monitored by TLC. After completion, the solvent was evaporated through rotavapour and the crude mixture was washed with dichloromethane-H2O and the organic phase was separated and dried over Na2SO4. The dichloromethane was evaporated followed by flash column purification on silica gel of the crude to obtain the pure products. The products were characterized using 1H, 13C NMR spectroscopy and GC-MS spectroscopy. The characterization data were in good agreement with those described in the literature.
71%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 120℃; for 12h;
62%	With sodium t-butanolate In 1,2-dimethoxyethane at 100℃; for 36h;

References: [1]Majumder, Arpi; Gupta, Ragini; Mandal, Mrinmay; Babu, Madhu; Chakraborty, Debashis [Journal of Organometallic Chemistry, 2015, vol. 781, p. 23 - 34].
[2]Heo, Yumi; Hyun, Dajung; Kumar, Manian Rajesh; Jung, Hyun Min; Lee, Sunwoo [Tetrahedron Letters, 2012, vol. 53, # 49, p. 6657 - 6661].
[3]Shen, Qilong; Ogata, Tokutaro; Hartwig, John F. [Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6586 - 6596].

18
[ 136-95-8 ]
[ 2012-74-0 ]
[ 1009206-06-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 493 - 498.

19
[ 136-95-8 ]
[ 878798-87-9 ]
[ 1235034-71-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
72%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;	tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2 (1H)-carboxylate (102) tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2 (1H)-carboxylate (102) To a stirred solution of 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (6.6 g, 23.80 mmol) (100) in DCM (100 mL) were added benzo[d]thiazol-2-amine (5.36 g, 35.70 mmol) (101), DCC(7.37 g, 35.70 mmol) and DMAP (8.72 g, 71.40 mmol). The reaction was stirred at room temperature for 16 h. The reaction mixture was quenched with water (200 mL) and extracted with DCM (3*150 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography on silica gel eluting with ethyl acetate in petroleum ether (0 to 30%) to afford tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2 (1H)-carboxylate (7.1 g, 72%) (102) as a white solid. 1H NMR (400 MHZ, DMSO-d6) δ 12.84 (s, 1H), 8.03 (d, J=7.2 Hz, 1H), 7.79 (d, J=8.0 Hz, 1H), 7.59 (dd, J=1.6, 7.4 Hz, 1H), 7.51-7.43 (m, 1H), 7.42-7.29 (m, 3H), 4.70 (s, 2H), 3.65-3.49 (m, 2H), 2.88 (t, J=6.0 Hz, 2H), 1.38 (s, 9H). ESI-MS [M+H]+calcd for (C22H23N3O3S): 410.15; found: 410.25.
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	1.1 To a solution of 2-(tert-butoxycarbonyl)- 1,2,3 ,4-tetrahydroisoquinoline-8- carboxylic acid (6.8 g, 24.5 mmol) and benzo[d]thiazol-2-amine (5.52 g, 36.8 mmol) in DCM (80 mL) was added EDCI (9.4 g, 49.04 mmol) and DMAP (6 g, 49 mmol). The mixture was stirred at rt overnight. The reaction mixture was diluted with DCM (400 mL), washed with 5% aq. HCl, water, brine, dried over Na2SO4, and concentrated under reduced pressure to provide 8.5 g of the desired product tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4- dihydroisoquinoline-2(lH)-carboxylate (IA): 1H NMR (300 MHz, CDCl3) δ ppm 7.83 (IH, m), 7.48 (IH, d), 7.34 (4H, m), 7.19 (IH, t), 4.91 (2H, m), 3.67 (2H, t), 2.92 (2H, t), 1.47 (9H, m). MS (ESI(+)): m/z 410 (M+H).

	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	1.1B tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate Example 1B tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate To a solution of 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (6.8 g) and benzo[d]thiazol-2-amine (5.52 g) in dichloromethane (80 mL) was added 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (9.4 g) and 4-dimethylaminopyridine (6 g). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (400 mL), washed with 5% aqueous HCl, water, and brine, and dried over Na2SO4. The mixture was filtered and the filtrate was concentrated under reduced pressure to provide the title compound.
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane	1.A tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate Example 1A tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate To a solution of 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (6.8 g) and benzo[d]thiazol-2-amine (5.52 g) in dichloromethane (80 mL) was added 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (9.4 g) and 4-dimethylaminopyridine (6 g). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (400 mL), washed with 5% aqueous HCl, water, and brine, and dried over Na2SO4. The mixture was filtered and the filtrate was concentrated under reduced pressure to provide the title compound.
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	5A tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(lH)-carboxylate 2-(?er?-Butoxycarbonyl)-l,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (6.7 g), benzo[i/]thiazol-2 -amine (5.5 g) and 4-dimethylaminopyridine (6.6 g) in dichloromethane (78 mL) were treated with l-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (9.3 g) at room temperature overnight. The reaction mixture was diluted with dichloromethane (450 mL) and washed with 3% aqueous HC1, water, and brine. The organic layer was dried over Na2S04, filtered and concentrated to provide the title compound.
8.5 g	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃;	1.2.7 1.2.7. tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4- dihydroisoquinoline-2(lH)-carboxylate To a solution of 2-(feri-butoxycarbonyl)-l,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (6.8 g) and benzo[
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	1.2.7 1.2.7. tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate To a solution of 2-(tert-butoxycarbonyl)- 1,2,3 ,4-tetrahydroisoquinoline-8 -carboxylic acid (6.8 g) and benzo[d]thiazol-2-amine (5.52 g) in dichloromethane (80 mL) was added 1-ethyl-3-[3- (dimethylanilno)propyl]-carbodiirnide hydrochloride (9.4 g) and 4-dimethylaminopyridine (6 g). Themixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (400 rnL), washed with 5% aqueous HCI, water, and brine, and dried over Na2504. The mixture was filtered, and the filtrate was concentrated under reduced pressure to provide the title compound.
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	1.2.7 1.2.7. tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate To a solution of 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (6.8 g) and benzo[d]thiazol-2-amine (5.52 g) in dichloromethane (80 mL) was added 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (9.4 g) and 4-dimethylaminopyridine (6 g). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (400 mL), washed with 5% aqueous HCl, water, and brine, and dried over Na2SO4. The mixture was filtered, and the filtrate was concentrated under reduced pressure to provide the title compound.
84 %	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	2.A Step A. tert-Butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)- carboxylate 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (6.5 g, 1 Eq, 23 mmol) was dissolved in dimethylformamide (30 mL). To the mixture was added HATU (11 g, 1.2 Eq, 28 mmol), followed by benzo[d]thiazol-2-amine (4.2 g, 1.2 Eq, 28 mmol) and N,N- diisopropylethylamine (4.5 g, 6.1 mL, 1.5 Eq, 35 mmol). The mixture was stirred at room temperature for overnight. The mixture was concentrated. The crude was extracted with ethyl acetate and water. The organic layer was separated and washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated to dryness. The crude was then purified by silica gel chromatography (ethyl acetate / hexane) to afford the title compound (8.1 g, 20 mmol, 84 % yield). MS (ESI) m/z: 410.2 [M+H]+
84 %	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	2.A Step A. tert-Butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)- carboxylate 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (6.5 g, 1 Eq, 23 mmol) was dissolved in dimethylformamide (30 mL). To the mixture was added HATU (11 g, 1.2 Eq, 28 mmol), followed by benzo[d]thiazol-2-amine (4.2 g, 1.2 Eq, 28 mmol) and N,N- diisopropylethylamine (4.5 g, 6.1 mL, 1.5 Eq, 35 mmol). The mixture was stirred at room temperature for overnight. The mixture was concentrated. The crude was extracted with ethyl acetate and water. The organic layer was separated and washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated to dryness. The crude was then purified by silica gel chromatography (ethyl acetate / hexane) to afford the title compound (8.1 g, 20 mmol, 84 % yield). MS (ESI) m/z: 410.2 [M+H]+

References: [1]Tao, Zhi-Fu; Hasvold, Lisa; Wang, Le; Wang, Xilu; Petros, Andrew M.; Park, Chang H.; Boghaert, Erwin R.; Catron, Nathaniel D.; Chen, Jun; Colman, Peter M.; Czabotar, Peter E.; Deshayes, Kurt; Fairbrother, Wayne J.; Flygare, John A.; Hymowitz, Sarah G.; Jin, Sha; Judge, Russell A.; Koehler, Michael F. T.; Kovar, Peter J.; Lessene, Guillaume; Mitten, Michael J.; Ndubaku, Chudi O.; Nimmer, Paul; Purkey, Hans E.; Oleksijew, Anatol; Phillips, Darren C.; Sleebs, Brad E.; Smith, Brian J.; Smith, Morey L.; Tahir, Stephen K.; Watson, Keith G.; Xiao, Yu; Xue, John; Zhang, Haichao; Zobel, Kerry; Rosenberg, Saul H.; Tse, Chris; Leverson, Joel D.; Elmore, Steven W.; Souers, Andrew J. [ACS Medicinal Chemistry Letters, 2014, vol. 5, # 10, p. 1088 - 1093].
[2]Current Patent Assignee: RUBEDO LIFE SCIENCES - US2025/171473, 2025, A1 Location in patent: Paragraph 0226-0227.
[3]Current Patent Assignee: GENENTECH - WO2010/80503, 2010, A1 Location in patent: Page/Page column 87-88.
[4]Current Patent Assignee: ABBVIE - US2013/96120, 2013, A1 Location in patent: Paragraph 0876.
[5]Current Patent Assignee: ABBVIE - US2013/96121, 2013, A1 Location in patent: Paragraph 1222.
[6]Current Patent Assignee: ABBVIE - WO2014/28381, 2014, A1 Location in patent: Page/Page column 111.
[7]Koehler, Michael F. T.; Bergeron, Philippe; Choo, Edna F.; Lau, Kevin; Ndubaku, Chudi; Dudley, Danette; Gibbons, Paul; Sleebs, Brad E.; Rye, Carl S.; Nikolakopoulos, George; Bui, Chinh; Kulasegaram, Sanji; Kersten, Wilhelmus J. A.; Smith, Brian J.; Czabotar, Peter E.; Colman, Peter M.; Huang, David C. S.; Baell, Jonathan B.; Watson, Keith G.; Hasvold, Lisa; Tao, Zhi-Fu; Wang, Le; Souers, Andrew J.; Elmore, Steven W.; Flygare, John A.; Fairbrother, Wayne J.; Lessene, Guillaume [ACS Medicinal Chemistry Letters, 2014, vol. 5, # 6, p. 662 - 667].
[8]Current Patent Assignee: ABBVIE - WO2016/94505, 2016, A1 Location in patent: Paragraph 000384.
[9]Current Patent Assignee: ABBVIE - WO2017/214456, 2017, A1 Location in patent: Page/Page column 279.
[10]Current Patent Assignee: ABBVIE - US2019/153107, 2019, A1 Location in patent: Paragraph 0861.
[11]Current Patent Assignee: TREELINE BIOSCIENCES - WO2023/215471, 2023, A1 Location in patent: Page/Page column 119-120.
[12]Current Patent Assignee: TREELINE BIOSCIENCES - WO2023/215471, 2023, A1 Location in patent: Page/Page column 119-120.

20
[ 136-95-8 ]
[ 591-50-4 ]
[ 1843-21-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1,10-Phenanthroline; copper(II) acetate monohydrate; caesium carbonate In dimethyl sulfoxide at 90℃; for 14h;
91%	With copper(l) iodide; potassium <i>tert</i>-butylate In 1,4-dioxane at 110℃; for 24h; Sealed tube;	1.1 Step 1 To a solution of benzo[d]thiazol-2-amine (LI) (1.00 g, 6.67 mmol) and anhydrous dioxane (8 mL) in a 50 mL glass sealed tube was added iodobenzene (LII) (1.50 g, 7.33 mmol), potassium /er/-butoxide (1.50 g, 13.3 mmol), and copper iodide (0.13 g, 6.67 mmol). The reaction mixture was sealed with a teflon screw cap, and heated to 1 l0°C with stirring for 24 h. After cooling to rt, brine (5 mL) was added and mixture was diluted with EtOAc (20 mL). The organic layer was dried over Na2S04, filtered, and concentrated under vacuum. Flash chromatography (1858) (EtOAc: hexanes, gradient elution from 0% EtOAc to 100% EtOAc) afforded 1.4 g (91%) of N-phenylbenzo[d]thiazol-2-amine (LIII). ESIMS found for C13H10N2S: mlz 227.6 (M+l).
83%	With Pd(tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide)(dibenzylideneacetone); caesium carbonate In isopropyl alcohol at 80℃; for 4h;	General experimental procedure for arylation of amines and phenols General procedure: To a stirred solution of aryl halide (1.2mmol) and [Pd(pp3S4)(dba)] (1mol %) in isopropanol (2.5ml) was added nitrogen/oxygen nucleophile (1mmol) followed by Cs2CO3 (2mol %) in the atmosphere of air. The mixture was heated to 80°C and the progress of the reaction was monitored by TLC. After completion, the solvent was evaporated through rotavapour and the crude mixture was washed with dichloromethane-H2O and the organic phase was separated and dried over Na2SO4. The dichloromethane was evaporated followed by flash column purification on silica gel of the crude to obtain the pure products. The products were characterized using 1H, 13C NMR spectroscopy and GC-MS spectroscopy. The characterization data were in good agreement with those described in the literature.

75%	With copper(l) iodide; potassium <i>tert</i>-butylate In 1,4-dioxane at 110℃; for 24h; Sealed tube; Inert atmosphere;	General Procedure for the coupling of Aryl Halides with Heteroarylamines General procedure: A 10 mL flask equipped with a Teflon valve was charged with a magnetic stir bar, CuI (2 mg, 1mol%), Heteroarylamine (1.5 mmol), KOtBu (224 mg, 2.0 mmol), solid aryl halides (1.0 mmol). The tube was evacuated and backfilled with argon. Under a counter flow of argon, dioxane (1.5mL), aryl halides (1.0 mmol, if liquid) were added by syringe. The tube was sealed. The reaction mixture was allowed to stir at 110 °C (X=I) or 130 °C (X= Br) for 24 h. Then the mixture was cooled to room temperature and added 5.0 mL brine. Subsequently, the mixture was extracted with ethyl acetate. The organic layers were collected, dried over Na2SO4, filtered and the solvent was removed under vacuum. The residue was purified by column chromatography on silica gel.
71%	With lanthanum(III) oxide; potassium hydroxide; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 110℃; for 12h; Inert atmosphere;
	With 1,10-Phenanthroline; potassium phosphate tribasic trihydrate; copper(II) acetate monohydrate; caesium carbonate In dimethyl sulfoxide at 90℃; for 14h;

References: [1]Boddapati, S. N. Murthy; Kurmarayuni, Chandra Mohan; Mutchu, Baby Ramana; Tamminana, Ramana; Bollikolla, Hari Babu [Organic and Biomolecular Chemistry, 2018, vol. 16, # 37, p. 8267 - 8272].
[2]Current Patent Assignee: RETROVIROX - WO2019/213295, 2019, A1 Location in patent: Paragraph 065; 066.
[3]Majumder, Arpi; Gupta, Ragini; Mandal, Mrinmay; Babu, Madhu; Chakraborty, Debashis [Journal of Organometallic Chemistry, 2015, vol. 781, p. 23 - 34].
[4]Wang, Deping; Kuang, Daizhi; Zhang, Fuxing; Liu, Yang; Ning, Shunhua [Tetrahedron Letters, 2014, vol. 55, # 51, p. 7121 - 7123].
[5]Murthy, S. Narayana; Madhav; Reddy, V. Prakash; Nageswar [Advanced Synthesis and Catalysis, 2010, vol. 352, # 18, p. 3241 - 3245].
[6]Boddapati, S. N. Murthy; Kurmarayuni, Chandra Mohan; Mutchu, Baby Ramana; Tamminana, Ramana; Bollikolla, Hari Babu [Organic and Biomolecular Chemistry, 2018, vol. 16, # 37, p. 8267 - 8272].

21
[ 136-95-8 ]
[ 1736-74-9 ]
[ 1307865-21-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With copper(l) chloride; sodium hydroxide In para-xylene at 130℃; for 12h; Inert atmosphere; regioselective reaction;
88 %	With tert-Amyl alcohol; [(p-cymene)Ru(2,2′-bpyO)(H₂O)]; caesium carbonate at 120℃; Schlenk technique; regioselective reaction;	4.2. General procedure for the regioselective N-alkylation of 2-aminobenzothiazoles with alcohols General procedure: To an oven-dried 25 mL Schlenk tube were added 2-aminobenzothiazole (1 mmol), alcohol (1.2 mmol), cat. 9 (2 mg,0.005 mmol, 0.5 mol %), Cs2CO3 (326 mg, 1 mmol, 1 equiv) and tertamylalcohol (1 mL). The mixture of reaction was heated under120 C in an oil bath for 12 h. The reaction mixture was cooledto ambient temperature, concentrated in vacuo and purified byflash column chromatography with ethyl acetate/hexanes to affordthe corresponding product.

References: [1]Li, Feng; Shan, Haixia; Kang, Qikai; Chen, Lin [Chemical Communications, 2011, vol. 47, # 17, p. 5058 - 5060].
[2]Xu, Xiangchao; Tang, Yawen; Zhang, Jin; Dong, Beixuan; Li, Feng [Journal of Catalysis, 2023, vol. 426, p. 21 - 29].

22
[ 136-95-8 ]
[ 29540-83-8 ]
[ 70785-26-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With t-BuBrettPhos; water; palladium diacetate; potassium carbonate In <i>tert</i>-butyl alcohol at 110℃; for 5h; Inert atmosphere;

References: [1]McGowan, Meredeth A.; Henderson, Jaclyn L.; Buchwald, Stephen L. [Organic Letters, 2012, vol. 14, # 6, p. 1432 - 1435].

23
[ 136-95-8 ]
[ 17890-55-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium hydroxide / water / 17 h / Reflux 1.2: 1 h / 20 °C 2.1: fluoroboric acid; sodium nitrite / water / 0.67 h / 0 - 5 °C 3.1: eosin y / dimethyl sulfoxide / 14 h / 20 °C / Irradiation

References: [1]Hari, Durga Prasad; Hering, Thea; Koenig, Burkhard [Organic Letters, 2012, vol. 14, # 20, p. 5334 - 5337,4].

24
[ 136-95-8 ]
[ 39539-66-7 ]
[ 1280873-18-8 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: we started with the4-methyl-1-piperazine carbonyl chloride (Scheme 1). By reactionof this compound with the corresponding amine in dry pyridineas solvent, at room temperature, the urea derivative crystallizedas hydrochloride. The hydrochloride was dissolved in water, basifiedwith aqueous Na2CO3 (10%) and extracted with CH2Cl2. The organiclayer was dried over Na2SO4 and the solvent was removed toafford a residue, which was purified by chromatography column toobtain the corresponding ureas 1-5.

References: [1]Journal of Molecular Structure,2013,vol. 1044,p. 215 - 220.

25
[ 136-95-8 ]
[ 1015248-96-0 ]
[ 1316861-19-4 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 6291 - 6296.
[2]Journal of Organic Chemistry,2013,vol. 78,p. 6291 - 6296.

26
[ 136-95-8 ]
[ 21815-91-8 ]
[ 330837-95-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	In acetone at 20℃; for 1h;
30%	With pyridine In acetone Reflux; Inert atmosphere;

References: [1]Naganagowda, Gadada; Petsom, Amorn [Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 1, p. 85 - 92].
[2]Brown, Ronald W.; Abdel-Megeed, Ashraf M.; Keller, Paul A.; Jones, Amy J.; Sykes, Melissa L.; Kaiser, Marcel; Baell, Jonathan B.; Avery, Vicky M.; Hyland, Christopher J. T. [RSC Medicinal Chemistry, 2020, vol. 11, # 12, p. 1413 - 1422].

27
[ 136-95-8 ]
[ 1900-41-0 ]
[ 1480489-66-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 2-amino-benzthiazole With sulfuric acid; sodium nitrite In acetic acid; propionic acid at 0 - 5℃; for 1.5h; Stage #2: 8-chloro-4-hydroxyquinolin-2(1H)-one With sodium hydroxide In water; acetic acid; propionic acid at 0 - 4℃; for 2h;	The general procedure for the synthesis and purification of disperse azo dyes General procedure: Nitrosyl sulfuric acid solution was prepared from concentrated sulfuric acid (1.5mL) and sodium nitrite (0.14g, 2mmol) at 70°C and then cooled to 5°C. This solution was added dropwise, with stirring, to 3mL of (acetic acid+propionic acid) mixture (5:1v/v) containing 2.0mmol of heterocyclic amines in an ice bath. The mixture was then stirred for 1.5h at about 0-5°C. After completion of diazotization procedure, the diazonium salt solution was added dropwise to the solution of 8-chloro 4-hydroxyquinoline -2-(1H)-one (0.39g, 2.0mmol) in sodium hydroxide (0.32g, 8.0mmol) and water (6.0ml). The resulting solution was vigorously stirred at about 0-4°C for 2h, while the pH of the reaction mixture was maintained 10-11 by adding 2.5% sodium hydroxide solution. The progress of the reaction was followed by TLC, using (ethyl acetate+petroleum ether) mixture (5:1 v/v) as solvent. Afterwards, the pH of reaction mixture was regulated 4-5 by means of a 10% hydrochloric acid solution. At the end of the procedure, the resulting solid was filtered, washed thoroughly with cold ethanol and dried. Recrystallization from DMF-H2O ended in pure crystals of the dye. The physical and spectral data of the purified dyes are as follows.

References: [1]Yahyazadeh, Asieh; Yousefi, Hessamoddin [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, vol. 117, p. 696 - 701].

28
[ 136-95-8 ]
[ 420-04-2 ]
[ 2582-07-2 ]

Yield	Reaction Conditions	Operation in experiment
31%	With scandium tris(trifluoromethanesulfonate) In 1,4-dioxane; water at 100℃; for 72h;	General Procedure for the Guanylation of Amines: General procedure: To a solution of p-methoxyaniline (1b, 61.6 mg, 0.50 μmol)and cyanamide (25.2 mg, 0.60 μmol) in H2O (2.5 mL) wasadded Sc(OTf)3 (24.6 mg, 50 nmol) at r.t. After the solutionwas stirred at 100 °C for 2 d, the resulting mixture waswashed with CHCl3 (3 × 10 mL). The aqueous layer wasconcentrated in vacuo, and the residue was purified by filtering through silica gel pad (CHCl3-MeOH, 20:1).

References: [1]Tsubokura, Kazuki; Iwata, Takayuki; Taichi, Misako; Kurbangalieva, Almira; Fukase, Koichi; Nakao, Yoichi; Tanaka, Katsunori [Synlett, 2014, vol. 25, # 9, p. 1302 - 1306].

29
[ 136-95-8 ]
[ 51934-39-5 ]
[ 1588534-71-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide

References: [1]Koehler, Michael F. T.; Bergeron, Philippe; Choo, Edna F.; Lau, Kevin; Ndubaku, Chudi; Dudley, Danette; Gibbons, Paul; Sleebs, Brad E.; Rye, Carl S.; Nikolakopoulos, George; Bui, Chinh; Kulasegaram, Sanji; Kersten, Wilhelmus J. A.; Smith, Brian J.; Czabotar, Peter E.; Colman, Peter M.; Huang, David C. S.; Baell, Jonathan B.; Watson, Keith G.; Hasvold, Lisa; Tao, Zhi-Fu; Wang, Le; Souers, Andrew J.; Elmore, Steven W.; Flygare, John A.; Fairbrother, Wayne J.; Lessene, Guillaume [ACS Medicinal Chemistry Letters, 2014, vol. 5, # 6, p. 662 - 667].

30
[ 136-95-8 ]
[ 7312-24-5 ]
[ 1588534-84-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 72h;

References: [1]Koehler, Michael F. T.; Bergeron, Philippe; Choo, Edna F.; Lau, Kevin; Ndubaku, Chudi; Dudley, Danette; Gibbons, Paul; Sleebs, Brad E.; Rye, Carl S.; Nikolakopoulos, George; Bui, Chinh; Kulasegaram, Sanji; Kersten, Wilhelmus J. A.; Smith, Brian J.; Czabotar, Peter E.; Colman, Peter M.; Huang, David C. S.; Baell, Jonathan B.; Watson, Keith G.; Hasvold, Lisa; Tao, Zhi-Fu; Wang, Le; Souers, Andrew J.; Elmore, Steven W.; Flygare, John A.; Fairbrother, Wayne J.; Lessene, Guillaume [ACS Medicinal Chemistry Letters, 2014, vol. 5, # 6, p. 662 - 667].

31
[ 136-95-8 ]
[ 39576-82-4 ]
[ 1781279-64-8 ]

Yield	Reaction Conditions	Operation in experiment
73%	With hydrogenchloride In isopropyl alcohol at 20℃;

References: [1]Mallikarjuna Reddy, Lingaladinne; Dinneswara Reddy, Guda; Padmaja, Adivireddy; Padmavathi, Venkatapuram [Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 75 - 80].

32
[ 136-95-8 ]
[ 105763-77-7 ]
N₂,N₄-di(benzo[d]thiazol-2-yl)-6-methoxyquinazoline-2,4-diamine [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2015,vol. 63,p. 75 - 80.

33
[ 136-95-8 ]
(1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-yl)(difluoromethylthio)silver [ No CAS ]
[ 943-08-8 ]

References: [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 7648 - 7652.
Angew. Chem.,2015,vol. 127,p. 7758 - 7762,5.

34
[ 136-95-8 ]
[ 64-18-6 ]
[ 4074-74-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tris(pentafluorophenyl)borate; phenylsilane In dibutyl ether at 100℃; Schlenk technique; Inert atmosphere;

References: [1]Fu, Ming-Chen; Shang, Rui; Cheng, Wan-Min; Fu, Yao [Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9042 - 9046][Angew. Chem., 2015, vol. 127, # 31, p. 9170 - 9174,5].

35
[ 867-44-7 ]
[ 136-95-8 ]
[ 2582-07-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	In ethanol; water for 16h; Reflux;	22 2.2.22. 1-(1,3-Benzothiazol-2-yl)guanidine (30) 2.2.22 1-(1,3-Benzothiazol-2-yl)guanidine (30) 2-Aminobenzothiazole (1 mmol) and S-methylisothiourea hemisulfate salt (1 mmol) was refluxed for sixteen hours in a mixture of ethanol/water (1:1), after which the solvent was removed under pressure to obtain the flaky solid. The crude product was boiled in water and treated with 0.5 M NaOH to bring pH of solution toward neutral, then allowed to cool gradually. White crude solid was obtained, it was recrystallized from ethanol to yield white crystalline needle shaped crystals. % yield = 72%, mp 214-216 °C; 1H NMR (400 MHz, DMSO-d6): δ 3.34 (s, 2H, NH2), 7.0 (m, 1H, Ar), 7.20 (m, 1H, Ar), 7.31 (t, 1H, J = 7.52 Hz, Ar), 7.46 (s, 2H, NH2), 7.63 (dd, 1H, J = 6.96 Hz, Ar). 13C NMR (100 MHz, DMSO-d6,) δ 78.81, 117.55, 120.61, 120.75, 125.24, 130.73, 152.64, 166.25; IR (KBr, cm-1): 3424, 3339, 1655, 1601, 1491, 1460, 1618; MS: (ESI) m/z [M+H]+ calcd for [C8H8N4S]+: 192.04; found: 193.14.

References: [1]Chikhale, Rupesh; Thorat, Sonali; Pant, Amit; Jadhav, Ankush; Thatipamula, Krishna Chary; Bansode, Ratnadeep; Bhargavi; Karodia, Nazira; Rajasekharan; Paradkar, Anant; Khedekar, Pramod [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 20, p. 6689 - 6713].

36
[ 136-95-8 ]
[ 357952-79-5 ]
[ 7067-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol Reflux;	4.1. General procedure for one-pot synthesis of 2-arylimidazo[2,1-b]benzothiazoles (4a-h) from ketones 1 General procedure: A mixture of appropriate methyl ketone 1 (5 mmol) and HTIB 2 (1.95 g, 5 mmol) in acetonitrile(20 mL) was heated under reflux for 2 h. Excess of acetonitrile was distilled off. The formationof α-TK was confirmed by TLC monitoring of the reaction mixture. Then a solution of2-amino-6-(substituted)benzothiazole 3 (5 mmol) in absolute ethanol (10 mL) was added dropwiseto the reaction mixture. The resultant reaction mixture was heated under reflux for 4-5 h.The progress of the reaction was accomplished by TLC using pet ether:ethyl acetate (8:2) as thesolvent system. After completion of the reaction, the excess of solvent was distilled in vacuo,and a solid product separated out on cooling. The solid thus separated was filtered, neutralizedwith aq. sodium bicarbonate solution, washed with water and purified by recrystallization fromethanol to afford 4. The spectroscopic data were consistent with literature.

References: [1]Sumran, Garima; Aggarwal, Ranjana [Journal of Sulfur Chemistry, 2015, vol. 36, # 2, p. 170 - 177].

37
[ 23612-48-8 ]
[ 136-95-8 ]
[ 100-52-7 ]
[ 1824040-69-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	at 80 - 85℃; for 3.5h;	General procedure for the synthesis of 7-azagramine analogues In a round-bottom flask containing a magnetic stirrer, a mixture of aldehyde (1 mmol) and heteroaryl amine (1 mmol) was placed andstirred at about 80-85 8C for 20 min. Then 2-methyl-7-azaindole(1 mmol) was added in portions, and the mixture was heated to 80-85 8C. Completion of the reaction was monitored by thin-layerchromatography (TLC) analysis. After completion, the reactionmixture was cooled to room temperature and a small quantity ofethanol was added. The solution was poured into ice-water, and theprecipitate formed was filtered, washed with an ice cold ethanol-water (1:1) mixture. The crude products were stirred in boiling nhexaneand filtered to afford the pure products.

References: [1]Dongare, Sakharam B.; Chavan, Hemant V.; Bhale, Pravin S.; Mule, Yoginath B.; Kotmale, Amol S.; Bandgar, Babasaheb P. [Chinese Chemical Letters, 2016, vol. 27, # 1, p. 99 - 103].

38
[ 23612-48-8 ]
[ 136-95-8 ]
[ 104-88-1 ]
[ 1824040-70-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	at 80 - 85℃; for 4h;	General procedure for the synthesis of 7-azagramine analogues In a round-bottom flask containing a magnetic stirrer, a mixture of aldehyde (1 mmol) and heteroaryl amine (1 mmol) was placed andstirred at about 80-85 8C for 20 min. Then 2-methyl-7-azaindole(1 mmol) was added in portions, and the mixture was heated to 80-85 8C. Completion of the reaction was monitored by thin-layerchromatography (TLC) analysis. After completion, the reactionmixture was cooled to room temperature and a small quantity ofethanol was added. The solution was poured into ice-water, and theprecipitate formed was filtered, washed with an ice cold ethanol-water (1:1) mixture. The crude products were stirred in boiling nhexaneand filtered to afford the pure products.

References: [1]Dongare, Sakharam B.; Chavan, Hemant V.; Bhale, Pravin S.; Mule, Yoginath B.; Kotmale, Amol S.; Bandgar, Babasaheb P. [Chinese Chemical Letters, 2016, vol. 27, # 1, p. 99 - 103].

39
[ 23612-48-8 ]
[ 136-95-8 ]
[ 874-42-0 ]
[ 1824040-71-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	at 80 - 85℃; for 4.5h;	General procedure for the synthesis of 7-azagramine analogues In a round-bottom flask containing a magnetic stirrer, a mixture of aldehyde (1 mmol) and heteroaryl amine (1 mmol) was placed andstirred at about 80-85 8C for 20 min. Then 2-methyl-7-azaindole(1 mmol) was added in portions, and the mixture was heated to 80-85 8C. Completion of the reaction was monitored by thin-layerchromatography (TLC) analysis. After completion, the reactionmixture was cooled to room temperature and a small quantity ofethanol was added. The solution was poured into ice-water, and theprecipitate formed was filtered, washed with an ice cold ethanol-water (1:1) mixture. The crude products were stirred in boiling nhexaneand filtered to afford the pure products.

References: [1]Dongare, Sakharam B.; Chavan, Hemant V.; Bhale, Pravin S.; Mule, Yoginath B.; Kotmale, Amol S.; Bandgar, Babasaheb P. [Chinese Chemical Letters, 2016, vol. 27, # 1, p. 99 - 103].

40
[ 23612-48-8 ]
[ 136-95-8 ]
[ 1550-35-2 ]
[ 1824040-72-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	at 80 - 85℃; for 3h;	General procedure for the synthesis of 7-azagramine analogues In a round-bottom flask containing a magnetic stirrer, a mixture of aldehyde (1 mmol) and heteroaryl amine (1 mmol) was placed andstirred at about 80-85 8C for 20 min. Then 2-methyl-7-azaindole(1 mmol) was added in portions, and the mixture was heated to 80-85 8C. Completion of the reaction was monitored by thin-layerchromatography (TLC) analysis. After completion, the reactionmixture was cooled to room temperature and a small quantity ofethanol was added. The solution was poured into ice-water, and theprecipitate formed was filtered, washed with an ice cold ethanol-water (1:1) mixture. The crude products were stirred in boiling nhexaneand filtered to afford the pure products.

References: [1]Dongare, Sakharam B.; Chavan, Hemant V.; Bhale, Pravin S.; Mule, Yoginath B.; Kotmale, Amol S.; Bandgar, Babasaheb P. [Chinese Chemical Letters, 2016, vol. 27, # 1, p. 99 - 103].

41
[ 23612-48-8 ]
[ 136-95-8 ]
[ 86-81-7 ]
[ 1824040-73-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	at 80 - 85℃; for 4h;	General procedure for the synthesis of 7-azagramine analogues In a round-bottom flask containing a magnetic stirrer, a mixture of aldehyde (1 mmol) and heteroaryl amine (1 mmol) was placed andstirred at about 80-85 8C for 20 min. Then 2-methyl-7-azaindole(1 mmol) was added in portions, and the mixture was heated to 80-85 8C. Completion of the reaction was monitored by thin-layerchromatography (TLC) analysis. After completion, the reactionmixture was cooled to room temperature and a small quantity ofethanol was added. The solution was poured into ice-water, and theprecipitate formed was filtered, washed with an ice cold ethanol-water (1:1) mixture. The crude products were stirred in boiling nhexaneand filtered to afford the pure products.

References: [1]Dongare, Sakharam B.; Chavan, Hemant V.; Bhale, Pravin S.; Mule, Yoginath B.; Kotmale, Amol S.; Bandgar, Babasaheb P. [Chinese Chemical Letters, 2016, vol. 27, # 1, p. 99 - 103].

42
[ 136-95-8 ]
[ 7120-13-0 ]
[ 1860826-70-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With tert.-butylnitrite; potassium acetate In 1,2-dichloro-ethane at 90℃; for 12h; Green chemistry;	2-(6-Phenylimidazo[2,1-b][1,3]thiazol-5-yl)-1,3-benzothiazole (3a); Typical Procedure General procedure: A 15-mL tube equipped with a Teflon cap and a magnetic stirring bar was charged with substrate 1a (0.20 mmol). 1,3-Benzothiazol-2-amine (2a; 0.40 mmol, 2.0 equiv), KOAc (0.20 mmol, 1.0 equiv), DCE (2 mL), and t-BuONO (0.40 mmol, 2.0 equiv) were then added sequentially. The tube was then capped and the mixture was stirred at 90 °C for 12 h. The crude mixture was diluted with EtOAc, filtered through a Celite pad, and washed with EtOAc. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography (silica gel, hexane-EtOAc) to give a yellow solid; yield: 52.2 mg (78%).

References: [1]Ji, Xiao-Ming; Xu, Li; Yan, Yun; Chen, Fan; Tang, Ri-Yuan [Synthesis, 2016, vol. 48, # 5, p. 687 - 696].

43
[ 136-95-8 ]
[ 7025-30-1 ]
[ 1860826-71-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With tert.-butylnitrite; potassium acetate In 1,2-dichloro-ethane at 90℃; for 12h; Green chemistry;	2-(6-Phenylimidazo[2,1-b][1,3]thiazol-5-yl)-1,3-benzothiazole (3a); Typical Procedure General procedure: A 15-mL tube equipped with a Teflon cap and a magnetic stirring bar was charged with substrate 1a (0.20 mmol). 1,3-Benzothiazol-2-amine (2a; 0.40 mmol, 2.0 equiv), KOAc (0.20 mmol, 1.0 equiv), DCE (2 mL), and t-BuONO (0.40 mmol, 2.0 equiv) were then added sequentially. The tube was then capped and the mixture was stirred at 90 °C for 12 h. The crude mixture was diluted with EtOAc, filtered through a Celite pad, and washed with EtOAc. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography (silica gel, hexane-EtOAc) to give a yellow solid; yield: 52.2 mg (78%).

References: [1]Ji, Xiao-Ming; Xu, Li; Yan, Yun; Chen, Fan; Tang, Ri-Yuan [Synthesis, 2016, vol. 48, # 5, p. 687 - 696].

44
[ 136-95-8 ]
[ 609-15-4 ]
[ 86932-98-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	In 1,4-dioxane for 24h; Reflux;
90%	With potassium carbonate In propan-2-one for 9h; Reflux;
83%	In ethylene glycol dimethyl ether at 90℃; for 6h;	2 4.1.2. Preparation of ethyl 2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxylate (2b) 2-Aminobenzothiazole (3.00 g, 19.97 mmol) and 2-chloroethylacetoacetate(3.30 mL, 23.96 mmol) were taken in 1,2-dimethoxyethane(30 mL) and heated at 90 C for 6 h. The reactionmixture was concentrated under reduced pressure, diluted withEtOAc (80 mL), washed the organic layer with H2O (3 30 mL).The separated organic layer was dried over anhyd Na2SO4 and concentratedunder vacuo to get crude compound. The crude compoundwas purified by column chromatography using 25% EtOAcin Hexanes as eluent to get ethyl 2-methylbenzo[d]imidazo[2,1-b]thiazole-3-carboxylate (2b) (4.32 g, 83%) as an Off-white solid.ESI-MS showed 261 [M+H]+ and carried to next step.

References: [1]Chitti, Surendar; Van Calster, Kevin; Cappoen, Davie; Nandikolla, Adinarayana; Khetmalis, Yogesh Mahadu; Cos, Paul; Kumar, Banoth Karan; Murugesan, Sankaranarayanan; Gowri Chandra Sekhar, Kondapalli Venkata [RSC Advances, 2022, vol. 12, # 35, p. 22385 - 22401].
[2]Al-Sultani; Al-Lami [Egyptian Journal of Chemistry, 2021, vol. 64, # 6, p. 2953 - 2961].
[3]Samala, Ganesh; Devi, Parthiban Brindha; Saxena, Shalini; Meda, Nikhila; Yogeeswari, Perumal; Sriram, Dharmarajan [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 6, p. 1298 - 1307].

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