N-benzyl-2-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide → 4-methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)-2,3-dihydro-1H-imidazol-1-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 17, making variations as required to replace N-benzyl-2-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide with 2-(5-hydroxy-2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide, the title compound was obtained as a colorless solid in 81% yield: mp 163-164° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.58-8.48 (m, 2H), 7.71-7.67 (m, 1H), 7.59 (d, J=8.1 Hz, 2H), 7.37 (d, J=8.1 Hz, 2H), 7.29-7.21 (m, 3H), 6.29 (d, J=3.3 Hz, 1H), 4.82 (s, 2H), 4.53 (d, J=5.7 Hz, 2H), 2.63 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.2, 153.5, 153.4, 150.5, 149.2, 148.9, 139.5, 135.8, 133.7, 130.8, 128.4, 128.1, 126.0, 122.0, 119.6, 113.1, 107.9, 46.9, 41.5, 17.3; MS (ES+) m/z 474.3 (M+1).

Provenance & Evidence