3-Fluorobenzoyl chloride → 2-(3-Fluorobenzoylamino)-4-methylthiazole-5-carboxylic Acid Benzylamide

HRID 45355

Reaction equation

HRID 45355 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH2:11]([NH:18][C:19]([C:21]1[S:25][C:24]([NH2:26])=[N:23][C:22]=1[CH3:27])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([NH:18][C:19]([C:21]1[S:25][C:24]([NH:26][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)=[N:23][C:22]=1[CH3:27])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 743763-Fluorobenzoyl chlorideHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Product 1

HCID 14682752-(3-Fluorobenzoylamino)-4-methylthiazole-5-carboxylic Acid BenzylamideYield 18%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 3-fluorobenzoyl 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 18% yield; m.p. 162-165° C.; 1H NMR (CDCl3, 300 MHz) δ 7.64-7.24 (m, 9H), 5.97 (t, J=5.4 Hz, 1H), 4.58 (d, J=5.4 Hz, 2H), 2.47 (s, 3H); MS (ES+) m/z 370.2 (M+1).

Sources & evidence

ORD record
ord-ea2233b0a96a48db928612f9c8a1b259
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

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