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

HRID 1785484Notes

Reaction equation

HRID 1785484 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.[NH3:30]>C(O)C>[CH3:21][O:20][C:18]1[C:17]([O:22][CH3:23])=[CH:16][C:15]2[N:11]([C:9]3[S:10][C:6]([C:4]([NH2:30])=[O:3])=[C:7]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:8]=3)[CH:12]=[N:13][C:14]=2[CH:19]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 24886662HCID 24886662, compound

Product 1

HCID 236544672-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid amideYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid amide was prepared from 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (80 mg, 0.20 mmol) and ammonia in ethanol (29 molar) as described above in the general amide formation procedure. The product was isolated by preparative HPCL: 7.7 mg, 36% yield. 1H-NMR (DMSO-D6) 8.78 (s, 1H); 7.80-7.90 (m, 4H); 7.789s, 1H); 7.40-7.55 (m, 3H); 7.38 (s, 1H); 3.84 (s, 3H); 3.83 (s, 3H). MS M/z 381 (M+1).

Workup

  1. customThe product was isolated by preparative HPCL

Sources & evidence

ORD record
ord-32c6f14ec2074983be4c1949f91105d3
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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