4-Methylmorpholine → N-benzyl-2-(4-bromobutanamido)-4-methylthiazole-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromobutyric acid (0.94 g, 5.50 mmol) and 4-methylmorpholine (0.70 mL, 6.20 mmol) in tetrahydrofuran (40 mL) was added isobutyl chloroformate (0.75 mL, 5.60 mmol) at 0° C. The resulting reaction mixture was stirred at 0° C. for 2 hours and then 2-amino-N-benzyl-4-methylthiazole-5-carboxamide (1.24 g, 5.00 mmol) was added. After 14 hours at ambient temperature, the solvent was removed in vacuo, and the residue was dissolved in ethyl acetate (200 mL), washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by column chromatography to yield the title compound (1.80 g, 90%): 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 5H), 5.99 (s, 1H), 4.57-4.55 (m, 2H), 4.34-4.27 (m, 2H), 3.38-3.44 (m, 2H), 2.64-2.18 (m, 5H); MS (ES+) m/z 396.3 (M+1) and 398.3 (M+1).

Provenance & Evidence