2,2-dimethoxy-N-(4-(trifluoromethyl)benzyl)ethanamine → 2-(3-(2,2-dimethoxyethyl)-3-(4-(trifluoromethyl)benzyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 2067313Notes

Reaction equation

HRID 2067313 reaction equation
[CH3:1][O:2]C(OC)CNC1C=CC(F)=CC=1.[CH3:15][O:16][CH:17]([O:31][CH3:32])[CH2:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1.[NH2:33][C:34]1[S:35][C:36]([C:40]([NH:42][CH2:43][C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)=[O:41])=[C:37]([CH3:39])[N:38]=1>>[CH3:32][O:31][CH:17]([O:16][CH3:15])[CH2:18][N:19]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][CH:22]=1)[C:1](=[O:2])[NH:33][C:34]1[S:35][C:36]([C:40]([NH:42][CH2:43][C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)=[O:41])=[C:37]([CH3:39])[N:38]=1

Participants

4

Reactant 3

HCID 606573432,2-dimethoxy-N-(4-(trifluoromethyl)benzyl)ethanamineHCID 627938962-amino-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideHCID 63686639N-(2,2-dimethoxyethyl)-4-fluoroaniline

Product 1

HCID 866452852-(3-(2,2-dimethoxyethyl)-3-(4-(trifluoromethyl)benzyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 52%

Procedure

Following the procedure as described in step B of Preparation 2, making variations as required to replace N-(2,2-dimethoxyethyl)-4-fluoroaniline with 2,2-dimethoxy-N-(4-(trifluoromethyl)benzyl)ethanamine to react with 2-amino-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide, 2-(3-(2,2-dimethoxyethyl)-3-(4-(trifluoromethyl)benzyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide was obtained in 52% yield: 1H NMR (300 MHz, CDCl3) δ 8.49 (d, J=1.5 Hz, 1H), 8.39-8.37 (m, 1H), 7.76-7.60 (m, 3H), 7.45 (d, J=8.1 Hz, 2H), 7.27 (d, J=8.1 Hz, 2H), 7.19-7.15 (m, 1H), 4.71-4.40 (m, 5H), 3.40 (d, J=4.8 Hz, 2H), 3.27 (s, 6H), 2.51 (s, 3H); MS (ES+) m/z 538.5 (M+1).

Workup

  1. customas described in step B of Preparation 2

Sources & evidence

ORD record
ord-85f6595f4094458aa94bf4e2c73a673a
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

Loading…