1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(azetidin-1-ylsulfonyl)-4-{[(5-chloro-6-isopropoxypyridin-3-yl)oxy]methyl}-2,5-difluorobenzamide

Participants

Reaction Steps

To a solution of 4-{[(5-chloro-6-isopropoxypyridin-3-yl)oxy]methyl}-2,5-difluorobenzoic acid (Preparation 15, 100 mg, 0.28 mmol) in dichloromethane (3 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (80 mg, 0.42 mmol) and 4-dimethylaminopyridine (51 mg, 0.42 mmol). The reaction was allowed to stir at room temperature for 20 minutes, before the addition of azetidine-1-sulfonamide (Preparation 19, 57 mg, 0.42 mmol). The reaction was stirred at room temperature for 18 hours. The solvent was removed in vacuo to leave a yellow solid. The crude material was dissolved in dimethylsulphoxide (2 mL) and purified twice by preparative HPLC to afford the title compound as a white powder (27 mg, 13%).

Provenance & Evidence