Cesium carbonate → N-Benzyl-4-methyl-2-(2-oxo-4-((5-phenyl-1,3,4-oxadiazol-2-yl)methoxy)pyridin-1(2H)-yl)thiazole-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide (0.20 g, 0.58 mmol) in anhydrous N,N-dimethylformamide (8 mL) was added cesium carbonate (0.32 g, 0.99 mmol) and catalytic amount of n-tetrabutylammonium iodide, followed by the addition of 2-(chloromethyl)-5-phenyl-1,3,4-oxadiazole (0.15 g, 0.76 mmol). The reaction mixture was heated at 80° C. for 20 hours and concentrated in vacuo, followed by the addition of dichloromethane (100 mL). The mixture was washed with water (70 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was concentrated in vacuo. The residue was recrystallized in ethyl acetate and hexane. The solid was collected by filtration and washed with methanol and hexanes to afford the title compound as a colorless solid in 38% yield (0.11 g): 1H NMR (300 MHz, DMSO-d6) δ 8.84 (t, J=5.9 Hz, 1H), 8.69 (d, J=8.0 Hz, 1H), 8.04-8.01 (m, 2H), 7.69-7.57 (m, 3H), 7.37-7.29 (m, 4H), 7.27-7.21 (m, 1H), 6.50-6.43 (m, 2H), 5.64 (s, 2H), 4.42 (d, J=5.9 Hz, 2H), 2.58 (s, 3H); MS (ES+) m/z 500.2 (M+1), 522.2 (M+23).

Provenance & Evidence