Benzylamine → 2-Bromo-N-(3,4-difluorobenzyl)-4-methylthiazole-5-carboxamide

HRID 2067322Notes

Reaction equation

HRID 2067322 reaction equation
C(N)C1C=CC=CC=1.[F:9][C:10]1[CH:11]=[C:12]([CH2:17][NH2:18])[CH:13]=[CH:14][C:15]=1[F:16].[Br:19][C:20]1[S:21][C:22]([C:26](O)=[O:27])=[C:23]([CH3:25])[N:24]=1>>[Br:19][C:20]1[S:21][C:22]([C:26]([NH:18][CH2:17][C:12]2[CH:13]=[CH:14][C:15]([F:16])=[C:10]([F:9])[CH:11]=2)=[O:27])=[C:23]([CH3:25])[N:24]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 1235723,4-DifluorobenzylamineHCID 28240582-Bromo-4-methyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 666311772-Bromo-N-(3,4-difluorobenzyl)-4-methylthiazole-5-carboxamideYield 61%

Procedure

Following the procedure as described in Preparation 8, making variations as required to replace benzyl amine with (3,4-difluorophenyl)methanamine to react with 2-bromo-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 61% yield: 1H NMR (300 MHz, CDCl3) δ 7.16-7.01 (m, 3H), 6.08-5.94 (m, 1H), 4.52 (d, J=5.9 Hz, 2H), 2.64 (s, 3H); MS (ES+) m/z 347.2 (M+1), 349.2 (M+3).

Workup

  1. customas described in Preparation 8

Sources & evidence

ORD record
ord-920e115b524944bf852c88ea4780e52d
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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