4-Fluorobenzylamine → N-(4-Fluorobenzyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 1, making variations only as required to use 4-fluorobenzylamine in place of benzylamine to react with 2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 37% yield: mp 280-282° C. (methanol/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 8.74 (t, J=5.9 Hz, 1H), 8.56 (d, J=8.0 Hz, 1H), 7.34-7.29 (m, 2H), 7.12 (t, J=8.9 Hz, 2H), 6.22 (dd, J=8.0, 2.5 Hz, 1H), 5.75 (d, J=2.5 Hz, 1H), 4.35 (d, J=5.8 Hz, 2H), 2.52 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.9, 162.0, 161.6, 154.1, 150.2, 139.9, 132.6, 128.7, 127.7, 127.2, 123.6, 104.4, 98.0, 43.1, 17.5; MS (ES+) m/z 360.1 (M+1).

Provenance & Evidence