1,2-Dichloroethane → 3-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)cyclopentanone

Participants

Reaction Conditions

Reaction Steps

To a slurry of 3-oxocyclopentanecarboxylic acid (0.123 g, 0.962 mmol) in DMF (1.0 ml) was added EDC (0.184 g, 0.962 mmol) followed by HOBT hydrate (0.130 g, 0.962 mmol). After about 1 h a solution of (Z)-3-chloro-N′-hydroxy-4-isopropoxybenzimidamide (0.2 g, 0.875 mmol) in DMF (0.5 ml) was added and the reaction mixture was heated to about 140° C. for about 45 min. After cooling to room temperature the reaction mixture was concentrated in vacuo and purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide 3-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)cyclopentanone (0.156 g, 56%) as a yellow oil. LCMS (Table 1, Method c) Rt=2.75 min, m/z 321 (M+H)+.

Provenance & Evidence