Phenylacetic Acid → N-benzyl-2-(5-benzyl-1,2,4-oxadiazol-3-yl)-4-methylthiazole-5-carboxamide

Participants

Reaction Steps

To a solution of phenylacetic acid (0.05 g, 0.37 mmol) in N,N-dimethylformamide (2 mL) was added 1,1′-carbonyldiimidazole (0.14 g, 0.83 mmol). The reaction mixture was stirred at ambient temperature for 1 hour, and N-benzyl-2-(N′-hydroxy-carbamimidoyl)-4-methylthiazole-5-carboxamide (0.12 g, 0.41 mmol) was added. The reaction mixture was stirred for 17 hours, diluted with dichloromethane, washed with water and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white powder (0.01 g, 6%): mp 124-125° C.; 1H NMR (300 MHz, CDCl3) δ 7.45-7.25 (m, 10H), 6.16 (t, J=5.6 Hz, 1H), 4.60 (d, J=5.6 Hz, 2H), 4.29 (s, 2H), 2.76 (s, 3H); MS (ES+) m/z 391.5 (M+1).

Provenance & Evidence