4-Fluorobenzylamine → 2-(3-benzyl-2-oxoimidazolidin-1-yl)-N-(2,4-difluorobenzyl)-4-methylthiazole-5-carboxamide

HRID 2067409Notes

Reaction equation

HRID 2067409 reaction equation
FC1C=CC(CN)=CC=1.[F:10][C:11]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14].[CH2:20]([N:27]1[CH2:31][CH2:30][N:29]([C:32]2[S:33][C:34]([C:38](O)=[O:39])=[C:35]([CH3:37])[N:36]=2)[C:28]1=[O:41])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([N:27]1[CH2:31][CH2:30][N:29]([C:32]2[S:33][C:34]([C:38]([NH:14][CH2:13][C:12]3[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:11]=3[F:10])=[O:39])=[C:35]([CH3:37])[N:36]=2)[C:28]1=[O:41])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 673264-FluorobenzylamineHCID 27332442,4-DifluorobenzylamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 250946012-(3-benzyl-2-oxoimidazolidin-1-yl)-N-(2,4-difluorobenzyl)-4-methylthiazole-5-carboxamideYield 45%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 4-fluorobenzylamine with 2,4-difluorobenzylamine to react with 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white powder in 45% yield: mp 157-158° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.39-7.23 (m, 6H), 6.84-6.74 (m, 2H), 6.06 (t, J=5.7 Hz, 1H), 4.53 (d, J=5.7 Hz, 2H), 4.49 (s, 2H), 4.03 (t, J=8.4 Hz, 2H), 3.43 (t, J=8.4 Hz, 2H), 2.57 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 164.1, 162.7, 160.8, 157.4, 155.3, 153.3, 135.5, 131.2, 128.9, 128.3, 128.0, 121.2, 117.0, 111.5, 103.9, 47.9, 42.0, 41.6, 37.4, 17.2; MS (ES+) m/z 443.2 (M+1).

Sources & evidence

ORD record
ord-205301e6bd494155b188283b8d7cedb0
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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