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

Participants

Reaction Steps

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).

Provenance & Evidence