1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[(E)-2-[{2-(1-benzylpiperidin-4-yl)ethyl}carbamoyl]vinyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole fumarate

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Reaction Steps

To a mixture of 3-{(E)-2-carboxyvinyl}-5-(4-cyanophenyl)-1,2,4-oxadiazole (0.25 g), 2-(1-benzylpiperidin-4-yl)ethylamine (0.23 g) and 1-hydroxybenzotriazole hydrate (0.16 g) in N,N-dimethylformamide (5 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.20 ml) at 5° C. After stirring for 1 hour at ambient temperature, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica eluting with 2% methanol in chloroform and the fractions containing the object compound were evaporated in vacuo. The residue was dissolved in a solution of fumaric acid (71 mg) in ethanol to give 3-[(E)-2-[{2-(1-benzylpiperidin-4-yl)ethyl}carbamoyl]vinyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole fumarate (0.32 g ).

Provenance & Evidence