1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Participants

Reaction Steps

To a solution of 2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid (0.20 g, 0.67 mmol) in anhydrous N,N-dimethylformamide (3 mL) was added 1-hydroxybenzotriazole (0.23 g, 1.73 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.17 g, 0.87 mmol), N,N-diisopropylethylamine (0.15 mL, 0.87 mmol) and pyridin-3-ylmethanamine (0.081 mL, 0.80 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with ethyl acetate (15 mL) and washed with saturated aqueous sodium bicarbonate (5 mL) and brine (5 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The obtained solid was washed with 5% ethyl acetate in hexanes and dried in air to afford the title compound as a white solid (0.16 g, 60%): mp 212-213° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.53 (br s, 1H), 7.98-7.95 (m, 1H), 7.73-7.66 (m, 1H), 7.43-7.22 (m, 6H), 6.28 (t, J=5.6 Hz, 1H), 5.55 (s, 2H), 4.61 (d, J=5.6 Hz, 2H), 2.67 (s, 3H); MS (ES+) m/z 391.3 (M+1).

Provenance & Evidence