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

HRID 1887245Notes

Reaction equation

HRID 1887245 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][NH2:10])[CH:5]=[CH:6][C:7]=1[F:8].FC1C=CC(CN)=CC=1.[Br:20][C:21]1[S:22][C:23]([C:27](O)=[O:28])=[C:24]([CH3:26])[N:25]=1>>[Br:20][C:21]1[S:22][C:23]([C:27]([NH:10][CH2:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)=[O:28])=[C:24]([CH3:26])[N:25]=1

Participants

4

Reactant 3

HCID 673264-FluorobenzylamineHCID 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 50%

Procedure

Following the procedure as described in Preparation 15, making variations only as requires to use (3,4-difluorophenyl)methanamine to replace (4-fluorophenyl)-methanamine to react with 2-bromo-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 50% 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 15

Sources & evidence

ORD record
ord-699b9465bccd409a8d485b8fde066a84
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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