2-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide → N-Benzyl-2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 3, making variations only as required to use 3-(benzyloxy)pyridin-2-ol in place of 4-aminopyridin-2(1H)-one to react with N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 7% yield: mp 198-201° C.; 1H NMR (300 MHz, CDCl3) δ 8.45 (dd, J=6.0, 3.0 Hz, 1H), 7.46-7.29 (m, 10H), 6.73 (d, J=6.0 Hz, 1H), 6.32 (t, J=6.0 Hz, 1H), 6.13 (br, 1H), 5.15 (s, 2H), 4.61 (d, J=6.0 Hz, 2H), 2.71 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 187.9, 162.1, 152.1, 148.9, 137.7, 135.5, 128.8, 128.7, 128.3, 127.8, 127.7, 127.3, 122.9, 114.8, 106.7, 106.7, 96.8, 71.1, 44.1, 17.3; MS (ES+) m/z 432.2 (M+1).

Provenance & Evidence