(+/-)-4-Aminopentanoic acid → HCID 89813151, compound

Participants

Reaction Steps

A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.16 mmole) and 4-amino-pentanoic acid (prepared from hydrolysis of 5-methyl-2-pyrrolidinone in 6 N HCl at reflux for 2 days, followed by lyophilization, 274 mg, 2.4 mmole) in 0.5 M sodium methoxide in methanol (4.6 ml) was refluxed for twenty hours before it was cooled to room temperature, concentrated and dissolved in water, extracted with dichloromethane. The remaining aqueous layer was acidified with 1N hydrochloric chloride, extracted with a mixture of dichloromethane and methanol. The organic layer was dried over anhydrous sodium sulfate, concentrated and purified by flash column chromatography on silica gel with a gradient of dichloromethane and methanol to give the title compound as a white solid (43 mg). LC-MS ESI−: 404 (M−1)−.

Provenance & Evidence