1-(Bromomethyl)-4-(trifluoromethyl)benzene → N-benzyl-4-methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)pyrrolidin-1-yl)thiazole-5-carboxamide

HRID 883147Notes

Reaction equation

HRID 883147 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH2:20][CH2:19][CH2:18][C:17]2=[O:21])=[N:13][C:12]=1[CH3:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1>>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH2:20][CH2:19][CH:18]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:29][CH:30]=3)[C:17]2=[O:21])=[N:13][C:12]=1[CH3:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 16954473N-benzyl-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 24801667N-benzyl-4-methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)pyrrolidin-1-yl)thiazole-5-carboxamideYield 27%

Procedure

Following the procedure as described in Example 2, making variation as required to use N-benzyl-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide in place of N-(4-fluorobenzyl)-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide to react with 1-(bromomethyl)-4-(trifluoromethyl)benzene, the title compound was obtained as a white solid in 27% yield: mp 174-175° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.54 (d, J=8.0 Hz, 2H), 7.39-7.20 (m, 7H), 6.01 (t, J=5.6 Hz, 1H), 4.57 (d, J=5.6 Hz, 2H), 4.14-4.02 (m, 1H), 3.93-3.79 (m, 1H), 3.35-3.24 (m, 1H), 3.09-2.96 (m 1H), 2.90-2.80 (m, 1H), 2.61 (s, 3H), 2.34-2.19 (m, 1H), 1.95-1.81 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 174.4, 162.3, 155.3, 152.6, 142.4, 137.8, 129.3, 128.8, 127.9, 127.7, 125.7, 125.6, 125.5, 118.8, 45.9, 44.2, 44.1, 36.2, 24.4, 17.2; MS (ES+) m/z 474.1 (M+1).

Sources & evidence

ORD record
ord-fb2d3be3776e4583a32e424a0ac33537
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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