3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole → HCID 86660295, compound

Participants

Reaction Steps

3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole (I45) (53.9 mg, 0.28 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(3-(methylcarbamoyl)-phenylamino)-2-phenylacetate (I10) (99 mg, 0.252 mmol) in a mixture of ethyl acetate (3.3 ml) and acetonitrile (1.7 ml). The reaction was stirred at room temperature for 2 days. Then the solution was evaporated and the residue was triturated with EtOAc (10 ml). The suspension was filtered on a buckner funnel, and the solid was recovered and further purified by flash chromatography (DCM/MeOH=85/15) to obtain (R)-3-(2-(3-(methylcarbamoyl)phenylamino)-2-phenylacetoxy)-1-((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-1-azoniabicyclo[2.2.2]octane chloride (23 mg, 15% yield, mixture of diastereomers).

Provenance & Evidence