Benzylamine → HCID 24958968, compound

Participants

Reaction Steps

To a solution of 1-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-1H-1,2,3-triazole-4-carboxylic acid (0.25 g, 0.73 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 1-hydroxybenzotriazole (0.12 g, 0.87 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.17 g, 0.87 mmol), N,N-diisopropylethylamine (0.38 mL, 2.19 mmol) and benzylamine (0.095 mL, 0.87 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with dichloromethane (30 mL) and washed with saturated aqueous sodium bicarbonate (15 mL) and brine (15 mL). The organic layer 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 solid in 8% yield: mp 178-180° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 9.33 (t, J=6.0 Hz, 1H), 9.24 (s, 1H), 9.02 (t, J=6.0 Hz, 1H), 7.36-7.23 (m, 10H), 4.49-4.46 (m, 4H), 2.63 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 160.1, 158.4, 154.2, 152.4, 143.6, 139.1, 138.9, 128.3, 128.2, 127.3, 127.2, 126.9, 126.8, 125.3, 123.5, 42.8, 42.1, 17.1; MS (ES+) m/z 433.3 (M+1).

Provenance & Evidence