1H-Indole-3-propanoic acid → HCID 22141354, compound

Participants

Reaction Steps

To a solution of 3-(1H-indol-3-yl)propanoic acid (235 mg, 1.2 mmol) in N,N-dimethylformamide (13 ml) was added 1-hydroxybenzotriazole monohydrate (200 mg, 1.31 mmol) and 1-(3-dimethylarninopropyl)-3-ethylcarbodiimide hydrochloride (340 mg, 1.77 numol). After stirring at room temperature for 5 min the mixture was treated with the hydrochloride salt of N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Preparation 53, 400 mg, 1.3 mmol) and sodium hydrogen carbonate (220 mg, 2.6 mmol). The reaction mixture was stirred at room temperature for 72 h before concentrating in vacua. Water (20 ml) was added and the reaction mixture was extracted with ethyl acetate (2×30 ml). The combined organic extracts were washed with water (20 ml) and saturated brine (20 ml), dried (MgSO4), filtered and concentrated in vacuo to give a pale yellow solid. The crude product was purified by shaking with dichloromethane (10 ml) and after filtration the filtrate was concentrated in vacuo to afford a pale yellow solid which was further purified by chromatography using a Sep-Pak™ cartridge packed with silica gel (10 g) eluting with dichoromethane:ethanol:0.88 ammonia (300:8:1) to afford the title compound as a white solid (235 mg, 43%).

Provenance & Evidence