m-Chloroperbenzoic acid → HCID 57744447, compound

Participants

Reaction Steps

To a stirred solution of 2-(4-methoxy-2-oxopyridin-1(2H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide (0.10 g, 0.28 mmol) in anhydrous dichloromethane (10 mL) was added m-chloroperoxy benzoic acid (0.072 g, 0.42 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 24 hours, diluted with dichloromethane (100 mL), washed with saturated bicarbonate solution (20 mL) and brine (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was crystallized in ethyl acetate and hexane. The solid was collected by filtration and washed with methanol and hexane to afford the title compound as a colorless solid in 34% yield (0.035 g): mp 255-257° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 8.81 (t, J=5.8 Hz, 1H), 8.59 (d, J=8.1 Hz, 1H), 8.13 (s, 1H), 8.09 (d, J=6.3 Hz, 1H), 7.37-7.23 (m, 2H), 6.33 (dd, J=8.1, 2.7 Hz, 1H), 6.12 (d, J=2.7 Hz, 1H), 4.34 (d, J=5.7 Hz, 2H), 3.81 (s, 3H), 2.54 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 168.6, 162.2, 161.7, 154.1, 151.0, 139.3, 138.1, 137.7, 131.9, 126.7, 124.9, 123.0, 104.2, 96.5, 56.8, 42.1, 17.5; MS (ES+) m/z 373.3 (M+1), 395.2 (M+23).

Provenance & Evidence