Diisopropylethylamine → N-Benzyl-2-(4-benzylbenzamido)-4-((diethylamino)methyl)thiazole-5-carboxamide

Participants

Reaction Steps

To a solution of 2-amino-N-benzyl-4-((diethylamino)methyl)thiazole-5-carboxamide (0.052 g, 0.16 mmol) and diisopropylethylamine (0.30 mL, 1.70 mmol) in dichloromethane (5 mL) was added 4-benzylbenzoic acid (0.046 g, 0.21 mmol) followed by the addition of N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.076 g, 0.20 mmol). The reaction mixture was stirred at ambient temperature for 18 h, diluted with ethyl acetate and washed with saturated sodium bicarbonate solution, brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by preparative HPLC (acetone/water gradient) to afford the title compound (0.003 g); MS (ES+) m/z 513.

Provenance & Evidence