1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 24958965, compound

Participants

Reaction Steps

To a solution of 4-methyl-2-(4-(3-phenylpropyl)-1H-1,2,3-triazol-1-yl)thiazole-5-carboxylic acid (4.62 g, 14.07) in anhydrous N,N-dimethylformamide (50 mL) was added 1-hydroxybenzotriazole (2.28 g, 16.88 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (3.24 g, 16.88 mmol), N,N-diisopropylethylamine (7.35 mL, 42.20 mmol) and pyridin-3-ylmethanamine (1.72 mL, 16.88 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with dichloromethane (150 mL) and washed with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white solid in 51% yield (3.00 g): mp 108-110° C. (dichloromethane/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 9.00 (t, J=6.0 Hz, 1H), 8.72 (s, 1H), 8.57 (s, 1H), 8.48 (d, J=6.0 Hz, 1H), 7.77-7.73 (m, 1H), 7.40-7.36 (m, 1H), 7.31-7.18 (m, 5H), 4.47 (d, J=6.0 Hz, 2H), 2.76-2.61 (m, 7H), 2.03-1.95 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 160.4, 155.1, 152.6, 148.8, 148.7, 148.2, 141.5, 135.2, 134.5, 128.3, 128.2, 125.7, 123.9, 123.5, 119.7, 40.6, 34.4, 30.1, 24.3, 17.1; MS (ES+) m/z 419.4 (M+1).

Provenance & Evidence