1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86703536, compound

Participants

Reaction Steps

To a mixture of 5-cyclopropyl-4-((4,4-difluoroadamantan-1-yl)-methoxy)-2-fluorobenzoic acid (0.25 g, 0.66 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.29 g, 1.51 mmol) and 4-dimethylaminopyridine (0.19 g, 1.51 mmol) in anhydrous dichloromethane (10 mL) was added azetidine-1-sulfonamide (0.13 g, 0.99 mmol) at ambient temperature. The resulting mixture was stirred at ambient temperature for 16 hours. The mixture was quenched with 1N hydrochloride acid (30 mL), followed by extraction with ethyl acetate (100 mL). The organic layer was washed with water (30 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo, the crude product was crystallized from ethyl acetate and hexanes and recrystallized from acetonitrile and water to afford the title compound as colorless solid (0.24 g, 73%): 1H NMR (300 MHz, DMSO-d6) δ 11.61 (s, 1H), 7.17 (d, J=8.3 Hz, 1H), 6.94 (d, J=12.9 Hz, 1H), 4.05 (t, J=7.7 Hz, 4H), 3.72 (s, 2H), 2.25-1.98 (m, 6H), 1.88-1.69 (m, 10H), 0.94-0.87 (m, 2H), 0.70-0.65 (m, 2H); MS (ES+) m/z 499.1 (M+1); MS (ES−) m/z 497.2 (M−1).

Provenance & Evidence