Pyridine → HCID 59369665, compound

Participants

Reaction Steps

To a cooled mixture of cyclopropylmethylamine (0.033 g, 0.46 mmol), pyridine (0.090 g, 1.14 mmol) and 4-dimethylaminoyridine (0.010 mg) in anhydrous tetrahydrofuran was added 2-benzoylamino-4-methylthiazole-5-carbonyl chloride (0.079 g, 0.038 mmol) in anhydrous dichloromethane (1 mL) dropwise. The reaction mixture was stirred at ambient temperature for 2 h, then diluted with dichloromethane (10 mL), washed with 1 N hydrochloric acid (5 mL), saturated aqueous sodium bisulfate (2×5 mL), and brine (5 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrate in vacuo and the residue was purified by column chromatography to afford the title compound as a white solid in 45% yield (45 mg); m.p. 163-166° C.; 1H NMR (CDCl3, 300 MHz) δ 7.89 (d, J=7.9 Hz, 2H), 7.57 (t, J=7.4 Hz, 1H), 7.45 (t, J=7.5 Hz, 2H), 5.84 (s, 1H), 3.23 (dd, J=5.4, 7.1 Hz, 2H), 2.23 (s, 3H), 1.00-0.98 (m, 1H), 0.53 (q, J=5.8 Hz, 2H), 0.22 (q, J=5.0 Hz, 2H); MS (ES+) m/z 316.1 (M+1).

Provenance & Evidence