Water → HCID 71523162, compound

Participants

Reaction Steps

2-(1-{2-[2-(2-oxopiperidin-1-yl)phenyl]ethyl}pyrrolidin-3-yl)benzoic acid a6-6 (0.31 g, 0.79 mmol, 1 eq) is dissolved in DMF and N,N′-carbonyldiimidazole (140 mg, 0.87 mmol, 1.1 eq) is added. The mixture is stirred at room temperature for 30 min, N-hydroxyacetamidine hydrochloride (95 mg, 0.87 mmol, 1.1 eq) is added and stirring is pursued for 4 hours. Another 1.1 eq of N,N′-carbonyldiimidazole and 1.1 eq of N-hydroxyacetamidine hydrochloride are added and the reaction mixture is stirred at reflux overnight. Dichloromethane and water are added and the organic layer is subsequently washed with water, HCl 1N, aqueous saturated NaHCO3 and brine. The organic layer is dried over MgSO4, evaporated and purified by preparative basic LC/MS (gradient: H2O/acetonitrile/NH4HCO3 0.5% w/v from 85/5/10 to 5/95/0 in 6.5 minutes) to afford 19 mg of 1-[2-(2-{3-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-1-yl}ethyl)phenyl]piperidin-2-one 11.

Provenance & Evidence