Triethylamine → 3-[5-(3-Methyl-2-piperidinyl)-1,2,4-oxadiazol-3-yl]benzonitrile

Participants

Reaction Conditions

Reaction Steps

2-[3-(3-cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-piperidine-1-carboxylic acid tert-butyl ester (150 mg, 14.7%) was obtained as described in Example 25 from 3-methyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (672 mg, 2.765 mmol) with triethylamine (1.1 g, 11 mmol) in THF (8 mL) with isobutyl chloroformate (377.6 mg, 2.765 mmol). After 30 minutes, 3-chloro-N-hydroxy-benzamidine (445 mg, 2.765 mmol) in DMF (5 mL) was added and then the reaction mixture was heated to 135° C. for 3 h. The product was purified by column chromatography with 5% ethyl acetate in hexanes. 3-[5-(3-methyl-piperidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile (85 mg, 77.8%) was obtained as described in Example 25 from 2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-piperidine-1-carboxylic acid tert-butyl ester (150 mg, 0.407 mmol) with trifluoroacetic acid (0.5 mL) and dichloromethane (4 mL) at room temperature for 2 h.

Provenance & Evidence