1-(Bromomethyl)-4-(trifluoromethyl)benzene → Ethyl 4-methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carboxylate

HRID 1882378Notes

Reaction equation

HRID 1882378 reaction equation
BrCC1CC1(F)F.[F:8][C:9]([F:19])([F:18])[C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1.[CH3:20][C:21]1[N:22]=[C:23]([N:31]2[CH2:35][CH2:34][NH:33][C:32]2=[O:36])[S:24][C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]>>[CH3:20][C:21]1[N:22]=[C:23]([N:31]2[CH2:35][CH2:34][N:33]([CH2:14][C:13]3[CH:16]=[CH:17][C:10]([C:9]([F:19])([F:18])[F:8])=[CH:11][CH:12]=3)[C:32]2=[O:36])[S:24][C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

4

Reactant 3

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 27614022-(Bromomethyl)-1,1-difluorocyclopropaneHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 57919795Ethyl 4-methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carboxylateYield 92%

Procedure

Following the procedure as described in Preparation 13, making variations to replace bromomethyl-2,2-difluorocyclopropane with 4-(trifluoromethyl)benzyl bromide to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 92% yield: mp 126-127° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.70 (d, J=8.1 Hz, 2H), 7.51 (d, J=8.1 Hz, 2H), 4.51 (s, 2H), 4.17 (q, J=6.9 Hz, 2H), 4.00 (t, J=8.1 Hz, 2H), 3.47 (t, J=8.1 Hz, 2H), 2.49 (s, 3H), 1.23 (t, J=6.9 Hz, 3H); MS (ES+) m/z 414.1 (M+1).

Workup

  1. customas described in Preparation 13

Sources & evidence

ORD record
ord-050ac04ff04849519ff50dec91b8f7a6
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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