N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid → 2-(2,5-Difluorobenzoylamino)-4-methylthiazole-5-carboxylic Acid Benzylamide

HRID 45328

Reaction equation

HRID 45328 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([NH2:27])=[N:24][C:23]=1[CH3:28])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([NH:27][C:4](=[O:5])[C:3]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:2]=2[F:1])=[N:24][C:23]=1[CH3:28])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 5880822,5-Difluorobenzoyl chloride

Product 1

HCID 593697032-(2,5-Difluorobenzoylamino)-4-methylthiazole-5-carboxylic Acid BenzylamideYield 86%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 2,5-difluorobenzoyl 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 86% yield; 1H NMR (DMSO-d6, 300 MHz) δ 8.63 (t, J=5.8 Hz, 1H), 7.60-7.17 (m, 8H), 4.36 (d, J=5.8 Hz, 2H), 2.51 (s, 3H); MS (ES+) m/z 388.2 (M+1).

Sources & evidence

ORD record
ord-5c691ab6129a4d9cb75df282ee905333
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

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