Triethylamine → N-benzyl-2-(5-bromopentanamido)-4-methylthiazole-5-carboxamide

Participants

Reaction Steps

To a mixture 2-amino-N-benzyl-4-methylthiazole-5-carboxamide (1.29 g, 5.20 mmol) and triethylamine (0.58 g, 5.72 mmol) in anhydrous dichloromethane (25.0 mL) was added dropwise 5-bromopentanoyl chloride (1.141 g, 5.72 mmol) in anhydrous dichloromethane (10 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 2 hours, then diluted with dichloromethane (40 mL) and washed with saturated aqueous sodium bicarbonate solution (2×50 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrate in vacuo to afford the title compound as a yellow oil (1.91 g, 92%): 1H NMR (300 MHz, CDCl3) δ 8.81 (br s, 1H), 7.33-7.23 (m, 5H), 5.91 (s, 1H), 4.14 (d, J=5.6 Hz, 2H), 3.51 (t, J=6.7 Hz, 2H), 2.46 (s, 3H), 2.35 (t, J=6.7 Hz, 2H), 1.82 (m, 2H), 1.53 (m, 2H); MS (ES+) m/z 410.1 (M+1), 412.1 (M+1).

Provenance & Evidence