2-(3-(2,2-dimethoxyethyl)-3-(4-(trifluoromethyl)benzyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide → 2-(5-hydroxy-2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 560734Notes

Reaction equation

HRID 560734 reaction equation
C(NC(C1SC(NC(N(CC(OC)OC)CC2C=CC(F)=CC=2)=O)=NC=1C)=O)C1C=CC=CC=1.CO[CH:37]([O:70]C)[CH2:38][N:39]([CH2:59][C:60]1[CH:65]=[CH:64][C:63]([C:66]([F:69])([F:68])[F:67])=[CH:62][CH:61]=1)[C:40](=[O:58])[NH:41][C:42]1[S:43][C:44]([C:48]([NH:50][CH2:51][C:52]2[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=2)=[O:49])=[C:45]([CH3:47])[N:46]=1>>[OH:70][CH:37]1[N:41]([C:42]2[S:43][C:44]([C:48]([NH:50][CH2:51][C:52]3[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=3)=[O:49])=[C:45]([CH3:47])[N:46]=2)[C:40](=[O:58])[N:39]([CH2:59][C:60]2[CH:65]=[CH:64][C:63]([C:66]([F:69])([F:68])[F:67])=[CH:62][CH:61]=2)[CH2:38]1

Participants

3

Reactant 2

HCID 866452852-(3-(2,2-dimethoxyethyl)-3-(4-(trifluoromethyl)benzyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideHCID 86645286N-benzyl-2-(3-(2,2-dimethoxyethyl)-3-(4-fluorobenzyl)ureido)-4-methylthiazole-5-carboxamide

Product 1

HCID 250956772-(5-hydroxy-2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 98%

Procedure

Following the procedure as described in Example 16, making variations as required to replace N-benzyl-2-(3-(2,2-dimethoxyethyl)-3-(4-fluorobenzyl)ureido)-4-methylthiazole-5-carboxamide with 2-(3-(2,2-dimethoxyethyl)-3-(4-(trifluoromethyl)-benzyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide, the title compound was obtained as a colorless solid in 98% yield: mp 171-172° C. (ethyl acetate/hexanes): 1H NMR (300 MHz, CDCl3) δ 8.45-8.42 (m, 2H), 7.69-7.62 (m, 2H), 7.57 (d, J=8.1 Hz, 2H), 7.34 (d, J=8.1 Hz, 2H), 7.27-7.22 (m, 1H), 6.08-6.05 (m, 1H), 4.56-4.37 (m, 4H), 3.65-6.59 (m, 1H), 3.33-3.25 (m, 1H), 2.51 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.6, 157.1, 154.0, 153.1, 148.4, 139.4, 135.8, 135.0, 134.2, 130.1, 128.6, 125.9, 123.7, 121.8, 117.5, 50.2, 46.9, 41.4, 17.2; MS (ES+) m/z 492.2 (M+1).

Sources & evidence

ORD record
ord-d1ec1b390e07471487ed6aa151a0e615
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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