6-oxo-N-phenyl-1H-pyridine-3-carboxamide → N-Benzyl-4-methyl-2-(2-oxo-5-(phenylcarbamoyl)pyridin-1(2H)-yl)thiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 3, making variations only as required to use 6-oxo-N-phenyl-1,6-dihydropyridine-3-carboxamide 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 colorless solid in 31% yield: mp 223-225° C. (hexane/ethyl acetate); 1H-NMR (300 MHz, DMSO-d6) δ 10.39 (s, 1H), 9.40 (d, J=2.5 Hz, 1H), 8.89 (t, J=5.9 Hz, 1H), 8.14 (dd, J=9.6, 2.5 Hz, 1H), 7.70-7.68 (m, 2H), 7.36-7.28 (m, 6H), 7.26-7.18 (m, 1H), 7.11-7.07 (m, 1H), 6.86 (d, J=9.6 Hz, 1H), 4.41 (d, J=5.9 Hz, 2H), 2.61 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.4, 161.6, 160.1, 153.5, 150.5, 139.7, 139.3, 139.1, 134.0, 129.1, 128.7, 127.7, 127.3, 125.3, 124.4, 121.0, 120.2, 116.2, 43.2, 17.5; (ES+) m/z 445.1 (M+1).

Provenance & Evidence