N-benzyl-2-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide → 2-(3-(4-fluorobenzyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl)-4-methyl-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-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide, the title compound was obtained as a colorless solid in 81% yield: mp 158-159° C. (ethyl acetate/hexanes): 1H NMR (300 MHz, CDCl3) δ 8.58 (d, J=1.5 Hz, 1H), 8.49 (dd, J=4.5, 1.5 Hz, 1H), 7.69-7.65 (m, 1H), 7.26-7.16 (m, 4H), 7.04-6.97 (m, 2H), 6.47 (t, J=5.7 Hz, 1H), 6.29 (d, J=3.3 Hz, 1H), 4.78 (s, 2H), 4.58 (d, J=5.7 Hz, 2H), 2.62 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.6, 162.2, 153.5, 150.5, 149.2, 149.0, 135.6, 133.7, 131.3, 129.8, 123.6, 119.5, 116.1, 115.8, 113.1, 107.6, 46.7, 41.5, 17.2; MS (ES+) m/z 424.3 (M+1).

Provenance & Evidence