N-Benzyl-2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide → N-Benzyl-2-(3-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

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A mixture of N-benzyl-2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide (0.14 g, 0.32 mmol) and 20 wt. % palladium on activated carbon (0.10 g) in methanol (50 mL) was stirred under an atmosphere of hydrogen for 2 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography followed by recrystallization from methanol (10 mL) to afford the title compound (0.027 g, 8%): mp 225-228° C.; 1H NMR (300 MHz, CD3OD) δ 8.63 (d, J=7.6 Hz, 1H), 7.42-7.26 (m, 5H), 6.20-6.10 (m, 1H), 5.87-5.83 (m, 1H), 4.36 (d, J=6.0 Hz, 2H), 2.58 (s, 3H); MS (ES+) m/z 342.2 (M+1).

Provenance & Evidence