3-(Trifluoromethyl)benzoyl chloride → 4-Methyl-2-(3-trifluoromethylbenzoylamino)thiazole-5-carboxylic Acid Benzylamide

HRID 45346

Reaction equation

HRID 45346 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH2:14]([NH:21][C:22]([C:24]1[S:28][C:27]([NH2:29])=[N:26][C:25]=1[CH3:30])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([NH:21][C:22]([C:24]1[S:28][C:27]([NH:29][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=2)=[N:26][C:25]=1[CH3:30])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Product 1

HCID 593696414-Methyl-2-(3-trifluoromethylbenzoylamino)thiazole-5-carboxylic Acid BenzylamideYield 27%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 3-trifluoromethylbenzoyl chloride in place of benzoyl chloride to react with 2-amino-4-methylthiazole-5-carboxylic acid benzylamide, the title compound was obtained as a white solid in 27% yield; m.p. 195-196° C.; 1H NMR (CDCl3, 300 MHz) δ 8.15 (s, 1H), 8.07 (d, J=7.8 Hz, 1H), 7.85 (d, J=7.8 Hz, 1H), 7.65 (t, J=7.8 Hz, 1H), 7.40-7.27 (m, 5H), 5.97 (t, J=4.7 Hz, 1H), 4.59 (d, J=5.5 Hz, 2H), 2.49 (s, 3H); MS (ES+) m/z 420 (M+1).

Sources & evidence

ORD record
ord-833bef35b9da4feda54ec1b06263ef98
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

Loading…