Triethylamine → N,4-Dibenzyl-2-(3-phenylpropanamido)thiazole-5-carboxamide

Participants

Reaction Steps

To a solution of 2-amino-N,4-dibenzylthiazole-5-carboxamide (0.053 g, 0.16 mmol) in tetrahydrofuran (5 mL) at 0° C. was added hydrocinnamoyl chloride (0.03 mL, 0.20 mmol), DMAP (cat.) and triethylamine (0.3 mL, 2.10 mmol). The reaction mixture was allowed to warm to ambient temperature over 18 h then concentrated in vacuo. The crude product was purified by flash column chromatography eluting with ethyl acetate/hexanes (5/95 to 100/0) to afford the title compound in 49% yield (0.036 g); 1H NMR (CDCl3, 400 MHz) δ 7.35-7.15 (m, 15H), 4.56 (d, J=5.6 Hz, 2H), 4.37 (s, 2H), 3.03 (t, J=7.6 Hz, 2H), 2.74 (t, J=7.6 Hz, 2H); MS (ES+) m/z 456 (M+1).

Provenance & Evidence