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

HRID 1785485Notes

Reaction equation

HRID 1785485 reaction equation
C([O:3][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)C.[CH3:30][NH:31][CH3:32]>CO>[CH3:30][N:31]([CH3:32])[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:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:3]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 248866622-(5,6-Dimethoxybenzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acid ethyl ester

Product 1

HCID 236544682-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid dimethylamide was prepared from 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (48.8 mg, 0.12 mmol) and dimethyl amine in methanol (2 molar) as described above in the general amide formation procedure. Product was isolated by preparative HPLC:15 mg, 30%. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.81 (s, 1 H); 7.84 (s, 1 H); 7.73-7.79 (m, 2H); 7.44-7.59 (m, 3 H); 7.40 (s, 1 H); 3.91 (s, 3 H, NCH3), 3.86 (s, 3 H); 3.01 (s, 3 H); 2.74 (s, 3 H). MS M/z 409 (M+1).

Workup

  1. customProduct was isolated by preparative HPLC

Sources & evidence

ORD record
ord-613b1935d1d64b12be7ea78814253fd8
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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