Triethylamine → HCID 68491830, compound

Participants

Reaction Steps

To a solution of 2-azido-N-benzyl-4-methylthiazole-5-carboxamide (0.53 g, 1.92 mmol) and ethyl acetoacetate (0.50 g, 3.85 mmol) in N,N-dimethylformamide (2 mL) was added triethylamine (0.54 mL, 3.85 mmol). The reaction mixture was stirred at ambient temperature for 24 hours, diluted with dichloromethane (30 mL) and washed with saturated aqueous sodium bicarbonate (5 mL) and brine (5 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white solid in 49% yield (0.36 g): 1H NMR (300 MHz, DMSO-d6) δ 9.03 (t, J=6.0 Hz, 1H), 7.36-7.34 (m, 5H), 4.46 (d, J=6.0 Hz, 2H), 4.35 (q, J=6.0 Hz, 2H), 2.89 (s, 3H), 2.64 (s, 3H), 1.34 (t, J=6.0 Hz, 3H); MS (ES+) m/z 386.3 (M+1).

Provenance & Evidence