[ CAS No. 124312-73-8 ] {[proInfo.proName]}

Name: 124312-73-8|(1-Methyl-1H-imidazol-2-yl)methanamine|98%
Brand: Ambeed
SKU: A915300
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Quality Control of [ 124312-73-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 124312-73-8 ]

SDS Specification

Alternatived Products of [ 124312-73-8 ]

Product Details of [ 124312-73-8 ]

CAS No. :	124312-73-8	MDL No. :	MFCD06660876
Formula :	C₅H₉N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PZSMLGOAJXSDMK-UHFFFAOYSA-N
M.W :	111.15	Pubchem ID :	533842
Synonyms :

Calculated chemistry of [ 124312-73-8 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.4
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.16
TPSA :	43.84 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.75 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.13
Log Po/w (XLOGP3) :	-1.09
Log Po/w (WLOGP) :	-0.27
Log Po/w (MLOGP) :	-0.94
Log Po/w (SILICOS-IT) :	-0.05
Consensus Log Po/w :	-0.24

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.24
Solubility :	64.1 mg/ml ; 0.577 mol/l
Class :	Very soluble
Log S (Ali) :	0.66
Solubility :	507.0 mg/ml ; 4.56 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.78
Solubility :	18.4 mg/ml ; 0.166 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 124312-73-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H317-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 124312-73-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 124312-73-8 ]
Downstream synthetic route of [ 124312-73-8 ]

[ 124312-73-8 ] Synthesis Path-Upstream 1~3

1
[ 1430413-09-4 ]
[ 124312-73-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; for 24 h; Autoclave	General procedure: In a stainless steel autoclave (20 mL), equipped with temperature control and magnetic stirrer, was purged 5 times with hydrogen, a solution of imine (3) (3.0 mmol) in CH₃OH with 5percent of Pd/C was transferred, the autoclave was pressurised at 20 atm and maintaining at room temperature. After 24 h, the mixture was filtered on celite and the solvent was evaporated with vacuum.

Reference： [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2379 - 2386

2
[ 13750-81-7 ]
[ 124312-73-8 ]

Reference： [1] Tetrahedron Letters, 2004, vol. 45, # 29, p. 5581 - 5583
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2379 - 2386

3
[ 864913-19-9 ]
[ 124312-73-8 ]

Reference： [1] Patent: EP1724263, 2006, A1, . Location in patent: Page/Page column 36-37

[ 124312-73-8 ] Synthesis Path-Downstream 1~38

Yield	Reaction Conditions	Operation in experiment
		Step A 2-Aminomethyl-1-methylimidazole To a suspension of lithium aluminum hydride (114 mg, 3.0 mmol) in dry tetrahydrofuran (15 mL) at room temperature in an inert atmosphere was added solid 1-methylimidazole-2-carboxamide (185 mg, 1.5 mmol) [prepared according to J. Org. Chem., 52, 4379 (1987)] in portions. After stirring the reaction mixture for 0.5 hour, the temperature was raised to 50° C. for 3.5 hours. After cooling this reaction, satd. aq. Na2 SO4 (2 mL) was added to quench reaction and then powdered anhyd. Na2 SO4. Filtration of this mixture to remove salts gave a dry solution of 2-aminomethyl-1-methylimidazole in tetrahydrofuran (~25 mL) which was used as is.

2
[ 124312-73-8 ]
[ 675583-72-9 ]
[1-(2-methoxymethoxy-5-methyl-phenyl)-1H-imidazol-4-ylmethylene]-(1-methyl-1H-imidazol-2-ylmethyl)-amine [ No CAS ]

Reference： [1]Chemical Communications,2004,p. 120 - 121

3
[ 13750-81-7 ]
[ 124312-73-8 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5581 - 5583
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2379 - 2386

4
[ 107819-90-9 ]
[ 124312-73-8 ]
[ 744202-36-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5581 - 5583

5
[ 3651-12-5 ]
[ 124312-73-8 ]
5-methyl-3,4-diphenyl-1H-pyrrole-2-carboxylic acid (1-methyl-1H-imidazol-2-ylmethyl)-amide [ No CAS ]

Reference： [1]Chemical Communications,2005,p. 3773 - 3775

6
N¹-(4-butylphenyl)-N³-(2-mercaptothiazolide)-isophthalamide [ No CAS ]
[ 124312-73-8 ]
N¹-(4-butylphenyl)-N³-((1-methyl-1H-imidazol-2-yl)methyl)-isophthalamide [ No CAS ]

Reference： [1]Chemical Communications,2007,p. 1736 - 1738

7
[ 94111-79-2 ]
[ 124312-73-8 ]
[ 941602-33-1 ]

Reference： [1]Chemical Communications,2007,p. 1736 - 1738

8
[ 124312-73-8 ]
[ 744202-40-2 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5581 - 5583

9
[ 124312-73-8 ]
C₁₉H₃₃N₅O₄Si^(2-) [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5581 - 5583

10
[ 124312-73-8 ]
2-Guanidinomethyl-3-methyl-3H-imidazole-4-sulfonic acid ((1S,2S)-2-benzyloxy-cyclopentyl)-amide; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5581 - 5583

11
[ 124312-73-8 ]
2-guanidinomethyl-3-methyl-3H-imidazole-4-sulfonic acid 3,5-bis-trifluoromethyl-benzylamide; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5581 - 5583

12
[ 913538-22-4 ]
[ 124312-73-8 ]
C₂₇H₂₈N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 190℃; for 0.25h;Microwave;	Fluoroquinolone (40 mg), 2-(methyamino)methyimidazole (0.05 ml), diisopropylethylamineamine (0.05 ml) and N-methylpyrrolidine were mixed and heated at 19O0C for 15min in a microwave reactor. The reaction was cooled, evaporated to a residue and purified on a reverse phase Cl 8 column using gradient elution using 0.1percent TFA in water and acetonitrile to yield 11 mg of product M+l+ 485. 1H NMR (CDCl3) delta 9.2 (s, IH), 7.86 (d, IH), 7.53 (d, IH), 7.37 (d, 2H), 7.31 (m, IH), 7.16 (m, IH), 7.06 (d, IH), 6.83 (d, IH), 4.92 (t, IH), 4.53 (d, 2H), 3.61 (q, 2H), 3.4 (s,3H) 2.74 (t, 2H), 2.6 (m, 4H), 1.80 (m, 4H).

Reference： [1]Patent: WO2006/113509,2006,A2 .Location in patent: Page/Page column 128

13
[ 864914-13-6 ]
[ 124312-73-8 ]
C₃₀H₄₂N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The compound (225 mg) obtained in Example 55-3 was dissolved in methanol (4.0 ml). The solution was added with the compound (64.5 mg) obtained in Example 14-7 and trimethyl orthoformate (0.13 ml) and the whole was stirred at room temperature for 1.5 hours. After having been cooled to 0°C, the reaction solution was added with sodium borohydride (20.8 mg) and the whole was stirred at room temperature for 20 minutes. After the reaction solution was concentrated under reduced pressure, the resultant residue was added with distilled water and the whole was subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with an anhydrous sodium sulfate. The drying agent was filtrated out and then the organic layer was concentrated under reduced pressure. The resultant was dissolved in methanol (6.0 ml). The reaction solution was added with 2-imidazole carboxaldehyde (83.3 mg) and sodium cyanoborohydride (77.3 mg). The whole was added with acetic acid to adjust the pH to 5 and stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure. The resultant residue was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and then the organic layer was concentrated under reduced pressure. The resultant residue was purified through silica gel column chromatography (hexane/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (174.3 mg) of the subject compound as a white solid. MS(FAB,Pos.):m/z=567[M+H]+ 1H-NMR(500MHz,DMSO-d6):delta=0.90(6H,t,J=7.3Hz),1.64-1.86(8H,m),2.95(4H,br),3.05(2H,br),3.28(2H,br),3.67(3H,s),3.83(2H,s),4.10(2H,s),4.17(2H,s),5.94(2H,s),7.31-7.39(5H,m),7.49-7.54(3H,m),7.60(2H,s),7.72(1H,d,J=8.4Hz),8.17(1H,s),10.43(1H,br),14.94(2H,br).

Reference： [1]Patent: EP1724263,2006,A1 .Location in patent: Page/Page column 81

14
C₁₉H₂₇N₃O₃ [ No CAS ]
[ 124312-73-8 ]
C₂₄H₃₆N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The compound (36.0 mg) obtained in Example 14-5 was dissolved inchloroform (0.6ml) andaddedwithmanganesedioxide (chemically processed product) (180 mg), and the whole was stirred at room temperature for 3 hours. After completion of the reaction, the solution was filtrated through Celite and the solvent was distilled off. The resultant was dissolved in anhydrous methanol (1.4 ml) and added with the compound (16.7 mg) obtained in Example 14-7 and trimethyl orthoformate (0.033 ml), and the whole was stirred at room temperature for 16 hours. Sodium borohydride (11.3 mg) was added thereto and the whole was stirred at room temperature for 4 hours, followed by addition of water. The solvent was distilled off under reduced pressure, followed by extraction with chloroform. The extract was dried with magnesium sulfate and the solvent was distilled off under reduced pressure. The resultant was dissolved in anhydrous methanol (1.2 ml) and added with 2-imidazole carboxaldehyde (14.4 mg) and sodium cyanoborohydride (18.9 mg). The solution was adjusted to pH 5 with acetic acid and stirred at room temperature for 2 days. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution and subjected to extraction with chloroform, followed by drying with magnesium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining a hydrochloride (19.4mg) of the subj ect compound as a white solid. MS(FAB,Pos.):m/z=521[M+H]+ 1H-NMR(500MHz,DMSO-d6+D2O):delta=0.87-0.90(6H,m),1.61-1.64(4H,m),1.79-1.83(4H,m),2.96-3.00(4H,m),3.07-3.08(2H,m),3.76(3H,s),4.03(1H,br),4.10(2H,br),4.24(4H,s),7.53-7.55(1H,m),7.61-7.63(4H,m),7.65(2H,s).

Reference： [1]Patent: EP1724263,2006,A1 .Location in patent: Page/Page column 37

15
C₁₉H₂₈N₄O₂ [ No CAS ]
[ 124312-73-8 ]
[ 864913-55-3 ]

Yield	Reaction Conditions	Operation in experiment
		A 15percent trimethyl aluminum/hexane solution (0.32 ml) was dropped into a dichloromethane solution (2.0 ml) containing the compound (72.0 mg) obtained in Example 1-2 and the wholewas stirred at room temperature for 15 minutes. A dichloromethane solution (2.0 ml) containing the compound (41.8 mg) obtained in Example 30-2 was dropped thereto and the whole was stirred at room temperature for 20 hours. To this solution, 1 mol/l hydrochloric acid was dropped to stop the reaction, and the whole was neutralized with a saturated aqueous sodium hydrogen carbonate solution and then subjected to extraction with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution and dried with anhydrous sodium sulfate. Of the resultant residue (65.2 mg), 40.2 mg thereof was dissolved in methanol (2.0 ml) and added with trimethyl orthoformate (0.040 ml). A methanol solution (1.0 ml) containing the compound (20.0 mg) obtained in Example 14-7 was dropped thereto and the whole was stirred at room temperature for 4 hours. After having been cooled to 0°C, the resultant was added with sodium borohydride (6.8 mg), warmed to room temperature, and stirred for 30 minutes. Water was added thereto to stop the reaction and the concentrated residue was extracted with chloroform. The organic layer was washed with water and a saturated saline solution and dried with anhydrous sodium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subj ect compound (34.7 mg) as a pale-yellow oily substance. MS(FAB,Pos.):m/z=440[M+H]+ 1H-NMR(500MHz,CDCl3):delta=0.86(6H,t,J=7.3Hz),1.43-1.48(4H,m),1.55-1.57(2H,m),1.63-1.66(2H,m),2.37(4H,t,J=7.3Hz),2.46(2H,br),3.48(2H,tt,J=6.3,6.9Hz),3.64(3H,s),3.85(2H,s),3.89(2H,s),6.82(1H,d,J=1.2Hz),6.94(1H,d,J=1.2Hz),7.26(1H,dd,J=1.7,9.3Hz),7.41(1H,t,J=5.8Hz),7.50(1H,d,J=9.3Hz),8.08(1H,d,J=0.6Hz),8.10(1H,d,J=1.1Hz).

Reference： [1]Patent: EP1724263,2006,A1 .Location in patent: Page/Page column 55-56

16
[ 864913-19-9 ]
[ 124312-73-8 ]

Yield	Reaction Conditions	Operation in experiment
	With water; hydrazine; In methanol; for 2.5h;Heating / reflux;	The compound (5.89 g) obtained in Example 14-6 was suspended in methanol (118 ml) and added with hydrazine monohydrate (1.89 ml), and the whole was refluxed under heating for 2.5 hours. After the solution was left for cooling, the precipitate was filtrated through Celite and the filtrate was distilled off under reduced pressure, thereby obtaining the subject compound (898.5 mg) as a yellow oily substance. MS(EI):m/z=111[M]+ 1H-NMR(500MHz,CDCl3):delta=1.99(2H,br),3.63(3H,s),3.90(2H,s),6.81(1H,d,J=1.2Hz),6.92(1H,d,J=1.2Hz).

Reference： [1]Patent: EP1724263,2006,A1 .Location in patent: Page/Page column 36-37

17
[ 56978-60-0 ]
[ 124312-73-8 ]
[ 1131736-18-9 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1 : 4-Amino-3,5-dichloro-iV-\|Yl -methyl- 1 H-imidazol-2- vOmethvpibenzenesulfonamide; 4-Amino-3,5-dichlorobenzenesulfonic acid (3.0 g, 12.4 mmol) was dissolved in thionyl chloride (18 mL) and DMF (0.3 mL). The reaction was warmed to 8O0C and stirred for four hours. The reaction was then cooled and the excess thionyl chloride was removed in vacuo azeotroping with toluene three times to afford the sulfonyl chloride. To a solution of the unpurified sulfonyl chloride (1.0 g, 3.84 mmol) in dichloromethane (7.7 mL) was added pyridine (0.9 mL, 11.5 mmol) and 1 -(I -methyl- lH-imidazol-2-yl)methanamine (1.3 g, 11.5 mmol). The reaction was stirred at room temperature for 18 hours and then quenched by the addition of sat. aq. NaHCO3 solution. The mixture was extracted with EtOAc and the organic extracts were dried over Na2SO4 and concentrated in vacuo. Purification of the residue by silica gel column chromatography (0-10percent MeOH/DCM) afforded the title compound.

Reference： [1]Patent: WO2009/35575,2009,A1 .Location in patent: Page/Page column 60

18
[ 1072925-09-7 ]
[ 124312-73-8 ]
[ 1138544-04-3 ]

Yield	Reaction Conditions	Operation in experiment
32%	With aluminum (III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20℃; for 3h;	EXAMPLE 13 To a solution of ester (750 mg, 1.83 mmol), <strong>[124312-73-8](1-methyl-1H-imidazol-2-yl)methanamine</strong> (0.50 mL, 4.50 mmol) and DBU (0.80 mL, 5.35 mmol) in DCM (50 mL) was added AlCl3 (750 mg, 5.62 mmol). The reaction mixture was stirred at rt for 3 h. The reaction was diluted with DCM (200 mL) and 3N NaOH (100 mL) and stirred for 10 min. The layers were separated and the organic layer was washed with H2O (2.x.100 mL), brine (100 mL), and dried over Na2SO4. The solvent was removed under reduced pressure and the reaction crude was purified on silica column (0-5percent MeOH/DCM) to yield the desired product as a white solid (275 mg, 32percent). 1H NMR (CDCl3) delta: 11.0 (t, 1H), 9.45 (d, 1H), 8.61 (d, 1H), 7.76 (dd, 1H), 7.50 (m, 1H), 7.45 (m, 1H), 6.99 (d, 1H), 6.90 (d, 1H), 6.83 (d, 1H), 4.82 (d, 2H), 3.93 (t, 4H), 3.81 (t, 4H), 3.70 (s, 3H). LCMS (ES): m/z 475 [M+1]+.

Reference： [1]Patent: US2009/93455,2009,A1 .Location in patent: Page/Page column 26

19
[ 1138544-08-7 ]
[ 124312-73-8 ]
[ 1138544-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20℃;	EXAMPLE 18 To a solution of ester (515 mg, 1.20 mmol) and <strong>[124312-73-8]C-(1-methyl-1H-imidazol-2-yl)-methylamine</strong> (199.5, 1.79 mmol) in DCM (40 mL) was added DBU (0.98 mL) and AlCl3 (352.3 mg). The reaction mixture was stirred at rt over night. The reaction was diluted with DCM (100 mL) and 6N NaOH (25 mL) and stirred for 10 min. The layers were separated and the organic layer was washed with H2O (2.x.50 mL), brine (50 mL), and dried over Na2SO4. The solvent was removed under reduced pressure and the resulting solid was triturated in ethyl acetate to give the desired product as a white solid. LCMS (ES): m/z 493 [M+1]+

Reference： [1]Patent: US2009/93455,2009,A1 .Location in patent: Page/Page column 28

20
[ 1333113-57-7 ]
[ 124312-73-8 ]
[ 1333113-58-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	With methanol; sodium tetrahydroborate; for 12h;	Using a similar procedure to that previously reported for bmima, 0.11 g (0.88 mmol) of 2-aminomethyl-1-methylimidazole and 0.19 g (0.90 mmol) of 8 in 25 mL of anhydrous MeOH was treated with 0.08 g (2 mmol) of NaBH4. Upon workup, 9 (0.18 g, 0.59 mmol) was obtained as a pale yellow oil. Yield: 67percent. 1H NMR CDCl3 delta 8.05 (s, AmIm(N-H)), 7.15 (s, AmIm(H-5)), 6.88 (s, 1, H-5), 6.77 (s, 1, H-4), 3.82 (s, 2, CH2), 3.77 (s, 2, AmIm(CH2)), 3.56 (s, 3, N-CH3), 3.52 (s, 3, AmIm(N-CH3)), 1.21 (s, 9, AmIm(C(CH3)3)). 13C NMR delta CDCl3 175.8 (s, C=O), 145.9 (s, AmIm(C4)), 141. 6 (s, Im(C2)), 136.2 (s, Im(C4)), 126.8 (s, Im(C5)), 121.8 (s, AmIm(C2)), 109.3 (s, AmIm(C5)), 44.7 (s, -CH2), 39.1 (s, AmIm(N-CH3)), 33.3 (s, Im(N-CH3)), (s, C(CH3)3), 27.8 (s, C(CH3)3). ESI-MS m/z 305.31 [M+H+].

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 4771 - 4774

21
[ 1333113-57-7 ]
[ 124312-73-8 ]
[ 885669-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium cyanoborohydride; at 20℃;	Method B. A solution of 8 (0.247 g, 1.17 mmol) in MeOH (20 mL) was treated sequentially with 2-aminomethyl-1-methylimidazole (0.059 g, 0.53 mmol) and NaBH3CN (0.07 g, 1 mmol). The reaction mixture was stirred at room temperature overnight and the solvent was removed under vacuum yielding L2 a yellow oil. The crude product was purified as described in method A with similar isolated yields. IR (KBr) 3052 cm-1 (amide-NH), 1667 cm-1 (amide-C=O); 1H NMR CD2Cl2 delta 7.81 (s, AmIm(N-H)), 7.09 (s, 2, AmIm(H-5)), 6.80 (s, 1, Im(H-5)), 6.75 (s, 1, Im(H-4)), 3.60 (s, 2, Im(-CH2)), 3.57 (s, 4, AmIm(CH2)), 3.07 (s, 3, Im(-CH3)), 3.02 (s, 6, AmIm(-CH3)), 1.18 (s, 18, AmIm(-C(CH3)3)). 13C NMR delta 174.1, 169.7 (s, AmIm(-C=O)), 145.4 (s,Im(C2)), 141.2 (s, AmIm(C2)), 135.5 (s, AmIm(C4)), 126.4 (s,Im(C5)), 120.8 (s, Im(C4)), 107.9 (s, AmIm(C-5)), 47.8 (s, Im(-CH2-), AmIm(-CH2-)), 38.0 (s, AmIm(C(CH3)3), 31.1 (s, Im(CH3)), 28.9 (s, AmIm(C(CH3)3); HRMS calcd for C25H40N9O2, 498.3305 [M+H+], found 498.3311.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 4771 - 4774

22
[ 124312-73-8 ]
[ 1338782-53-8 ]

Reference： [1]European Journal of Inorganic Chemistry,2011,p. 4161 - 4167

23
[ 124312-73-8 ]
[ 1338782-55-0 ]

Reference： [1]European Journal of Inorganic Chemistry,2011,p. 4161 - 4167

24
[ 124312-73-8 ]
[ 1338782-57-2 ]

Reference： [1]European Journal of Inorganic Chemistry,2011,p. 4161 - 4167

25
[ 124312-73-8 ]
[ 406486-57-5 ]
C₂₀H₂₆N₈O [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2011,p. 4161 - 4167

26
[ 1380343-07-6 ]
[ 124312-73-8 ]
[ 1380342-41-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	With potassium carbonate; In ethanol; at 100℃; for 16h;	2-Chloro-6-N-(7i-propyl)amino-[1,3,5]triazin-2-yl)-N,0-dimethyl- hydroxylamine (CD) (1 g, 4.5 mmol), (l-methyl-1H-imidazol-2-yl)methanamine (600 mg, 5.4 mmol) and KaC03 (1.24 g, 9 mmol) in EtOH (50 mL) were heated at 100 °C for 16 h. The reaction mixture was filtered, and the volatiles were removed under reduced pressure. The residue was dissolved in EtOAc (100 mL), washed with water (30 mL) and then with a brine solution (30 mL), and lastly dried over Na2S0 . The solvent was removed under reduced pressure. The crude product was purified by flash column chromatography (DCM MeOH=20/l to 8/1) to yield 4-N-(l-N- methylimidazol^-y^-methylamino-e-N-in-pro y amino-tl.S^Itriazin^-yl^NjO- dimethyl-hydroxylamine (CVII, 650 mg, 47percent).

Reference： [1]Patent: WO2012/74999,2012,A1 .Location in patent: Page/Page column 109

27
[ 10025-99-7 ]
[ 124312-73-8 ]
[ 1430412-81-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrogenchloride; In water; at 20℃;Reflux;	General procedure: To a solution of K2PtCl4 (0.208 g, 0.500 mmol) in 16 mL of H2O/HCl 4 M (ratio 15/1), the diamine (0.500 mmol) was added. The mixture was stirred for 6 h and heated under reflux, then it was warmed to room temperature and stirred overnight. The complex was filtered off and washed with water, methanol and diethyl ether. The solid was dried under vacuum at room temperature.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2379 - 2386

28
[ 1430413-09-4 ]
[ 124312-73-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 5%-palladium/activated carbon; hydrogen; In methanol; at 20℃; under 15201.0 Torr; for 24h;Autoclave;	General procedure: In a stainless steel autoclave (20 mL), equipped with temperature control and magnetic stirrer, was purged 5 times with hydrogen, a solution of imine (3) (3.0 mmol) in CH3OH with 5percent of Pd/C was transferred, the autoclave was pressurised at 20 atm and maintaining at room temperature. After 24 h, the mixture was filtered on celite and the solvent was evaporated with vacuum.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2379 - 2386

29
C₁₃H₁₇F₃N₂O₂ [ No CAS ]
[ 124312-73-8 ]
[ 1423767-16-1 ]

Reference： [1]ACS Combinatorial Science,2014,vol. 16,p. 303 - 308

30
(S)-1,1-bis-[3-(3-carboxymethoxy-phenyl)-propyl]-3-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-piperidinium chloride [ No CAS ]
[ 124312-73-8 ]
(S)-3-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-1,1-bis-[3-(3-[(1-methyl-1H-imidazol-2-ylmethyl)-carbamoyl]-methoxy}-phenyl)-propyl]-piperidinium hydroxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 10.11 (S)-3-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-1,1-bis-[3-(3-[(1-methyl-1H-imidazol-2-ylmethyl)-carbamoyl]-methoxy}-phenyl)-propyl]-piperidinium hydroxide (S)-1,1-Bis-[3-(3-carboxymethoxy-phenyl)-propyl]-3-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)amino]-piperidinium chloride (100 mg, 0.13 mmol),), <strong>[124312-73-8]C-(1-Methyl-1H-imidazol-2-yl)-methylamine</strong> (53 mg, 0.29 mmol) and N,N-Diisopropylethylamine (225 mul, 1.3 mmol) are dissolved in N,N-dimethylformamide (3.5 ml), 2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (93 mg, 0.29 mmol) is added. The reaction is stirred at room temperature overnight and purified by preparative HPLC-MS (MeOH/H2O+0.1percent TFA). The product is dissolved in dichloromethane, washed with a 2 molar potassiumcarbonate solution, dried over sodiumsulfate and concentrated in vacuo. LC (method L): tR=1.15 min; Mass spectrum (ESI+): m/z=841 [M]+. IC50=0.007
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	Example 10.11 : (S)-3-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]- 1 , 1 -bis- [3 -(3- [(1 -methyl- 1 H-imidazol-2-ylmethyl)-carbamoyl] -methoxy } -phenyl)-propyl] -piperidinium hydroxide Chiral (S)-l,l-Bis-[3-(3-carboxymethoxy-phenyl)-propyl]-3-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)- amino] -piperidinium chloride (100 mg, 0.13mmol), ), C-(l -Methyl- lH-imidazol-2-yl)-methylamine (53 mg, 0.29 mmol) and N,N-Diisopropylethylamine (225 mu, 1.3 mmol) are dissolved in N,N- dimethylformamide (3.5 ml), 2-(lH-Benzotriazol-l-yl)-l,l,3,3-tetramethyluronium tetrafluoroborate (93 mg, 0.29 mmol) is added. The reaction is stirred at room temperature overnight and purified by preparative HPLC-MS (MeOH/H20 + 0.1percent TFA). The product is dissolved in dichloromethane, washed with a 2 molar potassiumcarbonate solution, dried over sodiumsulfate and concentrated in vacuo. LC (method L): tR = 1.15 min; Mass spectrum (ESI+): m/z = 841 [M]+. IC50 = 0.007

Reference： [1]Patent: US2015/45326,2015,A1 .Location in patent: Paragraph 0239
[2]Patent: WO2015/18754,2015,A1 .Location in patent: Page/Page column 93

31
[ 124312-73-8 ]
7-chloro-2,5-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidine [ No CAS ]
2,5-dimethyl-N-((1-methyl-1H-imidazol-2-yl)methyl)-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 80℃; for 16h;Reflux;	General procedure: To a solution of 7-chloro-2,5-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidine (1 equiv) and diisopropylethylamine (1.5 equiv) in 2-propanol was added amine (1.2 equiv). After refluxing for 16 h, the reaction mixture was concentrated in vacuo and the appropriate solvent added to precipitate the crude product, which was collected by filtration and then purified by recrystallization, prep HPLC or column chromatography.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7240 - 7250

32
[ 136549-13-8 ]
[ 124312-73-8 ]
2,5-dimethyl-N-((1-methyl-1H-imidazol-2-yl)methyl)pyrazolo[1,5-a] pyrimidin-7-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 80℃; for 16h;Reflux;	General procedure: To a solution of 7-chloro-2,5-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidine (1 equiv) and diisopropylethylamine (1.5 equiv) in 2-propanol was added amine (1.2 equiv). After refluxing for 16 h, the reaction mixture was concentrated in vacuo and the appropriate solvent added to precipitate the crude product, which was collected by filtration and then purified by recrystallization, prep HPLC or column chromatography.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7240 - 7250

33
2-{2-[(1H-1,3-benzodiazol-2-ylmethyl)amino]ethyl}-1,3-thiazole-4-carboxylic acid [ No CAS ]
[ 124312-73-8 ]
2-{2-[(1H-1,3-benzodiazol-2-ylmethyl)amino]ethyl}-N-[(1-methyl-1H-imidazol-2-yl)methyl]-1,3-thiazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15 mg	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 dichloromethane; N,N-dimethyl-formamide; at 20℃; for 16h;	General procedure: To a stirring solution of 2-{2-[(1H-1,3-benzodiazol-2-ylmethyl)[(tert-butoxy)carbonyl]amino]ethyl}-1,3- thiazole-4-carboxylic acid (8) (3 g, 7.08 mmol), 1-(pyridin-2-yl)methanamine (1.1 ml, 10.62 mmol), DIPEA (3.7 ml, 21.24 mmol) and DMF (50 ml) at room temperature was added HATU (5.39 g, 14.16 mmol). The reaction mixture was allowed to stir at room temperature for 16 h. The reaction was diluted with EtOAc (100 ml) and washed with sat. NaHCQ (3 x 50 ml) and brine (3 x 50 ml). The organic layer was separated, dried (MgS04), filtered and evaporated to dryness. The crude residue was purified by flash column chromatography (kp-NH, eluting with a gradient of 20-100percent EtOAc in heptane) and then azeotroped with heptane to give the title compound (2.2 g, 62percent) as a yellow foam. 1H-NMR (MeOD, 500 MHz): d[ppm]= 8.49 (d, J = 4.4 Hz, 1H), 8.10 (s, 1H), 7.80 (td, J = 7.8, 1.7 Hz, 1H), 7.54 (s, 2H), 7.42 (d, J = 7.9 Hz, 1H), 7.31 (dd, J = 7.1, 5.2 Hz, 1H), 7.26- 7.20 (m, 2H), 4.75 (d, J = 12.3 Hz, 2H), 4.70 (s, 2H), 3.92-3.79 (m, 2H), 3.36 (d, J = 8.1 Hz, 1H), 1.43- 1.25 (m, 10H) HPLCMS (Method D): [m/z]: 493.1 [M+H]+In a similar fashion to general procedure 6, 2-{2-[(1 H-1 ,3-benzodiazol-2-ylmethyl)amino]ethyl}-1 ,3-thiazole- 4-carboxylic acid (80) (200 mg, 0.33 mmol, 50percent purity), 1-(1 -methyl-1 H-imidazol-2-yl)methanamine (36 mg, 0.33 mmol), DIPEA (230 muIota, 1.32 mmol) and HATU (189 mg, 0.496 mmol) in DCM (5 ml) and DMF (1 ml) afforded the title compound (15 mg, 12percent) after purification by basic prep-HPLC. 1 H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.09 (s, 1 H), 7.53 (dd, J = 5.9, 3.2 Hz, 2H), 7.26- 7.20 (m, 2H), 7.03 (d, J = 1.1 Hz, 1 H), 6.89 (d, J = 1.2 Hz, 1 H), 4.66 (s, 2H), 4.08 (s, 2H), 3.73 (s, 3H), 3.25 (t, J = 6.7 Hz, 2H), 3.1 1 (t, J = 6.7 Hz, 2H) HPLCMS (Method B): [m/z]: 396.2 [M+H]+

Reference： [1]Patent: WO2017/68089,2017,A2 .Location in patent: Page/Page column 138; 186; 187

34
2-(2-(thiophen-2-yl)-1H-indol-1-yl)acetic acid [ No CAS ]
[ 124312-73-8 ]
C₁₉H₁₈N₄OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2695 - 2701

35
[ 407-25-0 ]
[ 124312-73-8 ]
2,2,2-trifluoro-1-(1-methyl-5-(trifluoromethyl)-1H-imidazo[1,5-a]imidazol-7-yl)ethan-1-one [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 6578 - 6581

36
(1S,2S)-1-(4-methylbenzyl)-2-phenylcyclopropanecarboxylic acid [ No CAS ]
[ 124312-73-8 ]
(1R,2S)-1-N-((1-methyl-1H-imidazol-2-yl)methyl)-1-(4-methylbenzyl)-2-phenylcyclopropane-1-carboxamide [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2019,vol. 34,p. 31 - 43

37
[ 257640-86-1 ]
[ 124312-73-8 ]
9-fluoro-7-hydroxy-3-methyl-N-((1-methyl-1H-imidazol-2-yl)methyl)-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 132 - 136

38
[ 728034-12-6 ]
[ 165806-95-1 ]
[ 124312-73-8 ]
4-(4-(4-fluorophenyl)-1-((1-methyl-1H-imidazol-2-yl)methyl)-1H-imidazol-5-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used

Reference： [1]Patent: WO2019/185631,2019,A1 .Location in patent: Page/Page column 14; 90

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[ 124312-73-8 ]

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H200	Unstable explosive
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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