Water → 2-(4-Benzamido-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamide

Participants

Reaction Steps

To a mixture of 2-(4-amino-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamide (0.17 g, 0.50 mmol) and 4-dimethylaminopyridine (0.01 g) in pyridine (10 mL) was added benzoyl chloride (0.07 mL, 0.60 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 6 hours, and water (100 mL) was added. The title compound was precipitated as a solid which was collected by filtration and washed with water and t-butylmethyl ether (0.17 g, 76%): mp 246-248° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.66 (s, 1H), 8.78 (t, J=5.7 Hz, 1H), 8.67 (d, J=7.8 Hz, 1H), 7.95-7.90 (m, 2H), 7.66-7.47 (m, 3H), 7.35-7.18 (m, 6H), 6.94 (dd, J=7.8, 2.1 Hz, 1H), 4.39 (d, J=5.7 Hz, 2H), 2.55 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.4, 161.9, 161.0, 153.8, 150.3, 149.4, 139.8, 134.1, 132.9, 131.6, 129.0, 128.7, 128.4, 127.7, 127.2, 123.9, 104.2, 103.9, 43.1, 17.5; MS (ES+) m/z 445.3 (M+1).

Provenance & Evidence