Trifluoroacetic acid → 2-Benzoimidazol-1-yl-4-phenyl-thiazole-5-carboxylic acid amide

HRID 1785482Notes

Reaction equation

C([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)C.[OH-].[NH4+:27].FC(F)(F)C(O)=O>>[N:11]1([C:9]2[S:10][C:6]([C:4]([NH2:27])=[O:3])=[C:7]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:8]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[CH:12]1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 14923Ammonium Hydroxide

HCID 575958492-Benzoimidazol-1-yl-4-phenyl-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 236543872-Benzoimidazol-1-yl-4-phenyl-thiazole-5-carboxylic acid amideYield 13%

Procedure

2-Benzoimidazol-1-yl-4-phenyl-thiazole-5-carboxylic acid amide was prepared from 2-Benzoimidazol-1-yl-4-phenyl-thiazole-5-carboxylic acid ethyl ester (75 mg, 0.21 mmol) and ammonium hydroxide as described above in the general amide formation procedure. Preparative HPLC with trifluoroacetic acid, 9.1 mg, 13% yield. MS M/z 321 (M+1).

Sources & evidence

ORD record: ord-bb4775cc5c1145c0a1255bd2f894cd37
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504513B2

Reaction notes

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