Sodium hydride → HCID 44476404, compound

Participants

Reaction Steps

A mixture of 3-azetidinecarboxylic acid (Aldrich; 27.8 mg, 0.275 mmol), sodium hydride (60%; 8.79 mg, 0.220 mmol) in dimethyl sulfoxide (DMSO) (2 ml) was stirred at room temperature for 30 mins. 1-Chloro-5-(5-{3-chloro-4[(1methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)isoquinoline (D7; 44 mg, 0.110 mmol) was then added and the reaction mixture was heated to 120° C. under nitrogen overnight. The cooled reaction mixture was loaded onto a 10 g SCX column and eluted with acetonitrile followed by 10% ammonia in acetonitrile. The ammonia fractions were combined and evaporated and the residue was dissolved in dichloromethane and then washed with water. The organic phase was passed through a hydrophobic frit and the solvent was removed in vacuo to give the title compound as a yellow solid (9 mg)

Provenance & Evidence