Cyclopropylamine → 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid cyclopropylamide

HRID 1785490Notes

Reaction equation

HRID 1785490 reaction equation
C(O[C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([O:22][CH3:23])[C:18]([O:20][CH3:21])=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:5])C.[CH:30]1([NH2:33])[CH2:32][CH2:31]1>CO>[CH:30]1([NH:33][C:4]([C:6]2[S:10][C:9]([N:11]3[C:15]4[CH:16]=[C:17]([O:22][CH3:23])[C:18]([O:20][CH3:21])=[CH:19][C:14]=4[N:13]=[CH:12]3)=[N:8][C:7]=2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:5])[CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 24886662HCID 24886662, compound

Product 1

HCID 236544702-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid cyclopropylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid cyclopropylamide was prepared from 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (24 mg, 0.06 mmol) and cyclopropylamine in methanol (4 molar) as described above in the general amide formation procedure. Product was isolated by preparative HPLC: 10 mg, 40%. 1H-NMR (DMSO-D6) 8.8 (s, 1H); 8.54 (t, 1H); 7.80-7.87 (m, 2H), 7.41-7.55 (m, 3H); 7.38 (s, 1H); 3.90 (s, 3H); 3.86 (s, 3H); 3.25 (q, 2H); 1.08 (t, 3H). MS M/z 421 (M+1).

Workup

  1. customProduct was isolated by preparative HPLC

Sources & evidence

ORD record
ord-ce90a2564f46480babd0cc3e1ace11c7
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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