1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(Benzo[b]thiophen-2-ylmethyl)-2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Participants

Reaction Steps

To a solution of 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid (0.20 g, 0.58 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added N,N-diisopropylethylamine (0.27 g, 2.10 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.18 g, 0.93 mmol). The mixture was stirred for 30 minutes, followed by the addition of 1-hydroxybenzotriazole (0.11 g, 0.81 mmol) and benzo[b]thiophen-2-ylmethanamine (0.14 mL, 0.87 mmol). The reaction mixture was stirred at ambient temperature for 24 hours. The solvent was removed in vacuo and the residue was dissolved in dichloromethane (50 mL), washed with saturated aqueous sodium bicarbonate (2×5 mL) and brine (10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was recrystallized from ethyl acetate and hexane. The solid was collected by filtration and washed with methanol and hexane. The title compound was obtained as a colorless solid in 78% yield (0.22 g): 1H NMR (300 MHz, DMSO-d6) δ 8.98 (t, J=5.8 Hz, 1H), 8.61 (d, J=8.1 Hz, 1H), 7.82-7.85 (m, 1H), 7.76-7.73 (m, 1H), 7.51-7.23 (m, 8H), 6.34 (dd, J=8.1, 2.7 Hz, 1H), 6.23 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.65-4.63 (m, 2H), 2.56 (s, 3H); MS (ES+) m/z 488.1 (M+1).

Provenance & Evidence