1,3-Cyclohexanedione → HCID 59825691, compound

Participants

Reaction Steps

A mixture of 3-amino-2-ethoxycarbonyl-pyrrole (0.204 g, 1.32 mmol), 5-(5-chloro-6-methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (0.388 g, 1.32 mmol) and 1,3-cyclohexanedione (0.149 g, 1.32 mmol) in 10 ml of 1-butanol is heated at reflux temperature for 4 h. The reaction mixture is then concentrated under reduced pressure and purified on a silica gel column (34 g) eluted with a mixture of cyclohexane and ethylacetate (7/3, v/v). The fractions containing the expected product are concentrated under reduced pressure, and the residue is resuspended in 5 ml of acetonitrile and heated at reflux temperature for 15 minutes. After cooling to room temperature, the insoluble material is collected by filtration and dried under vacuum to yield 76 mg of 9-[5-(5-chloro-6-methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester. Yield=11%. Analytical LC/MS (method B): m/z=523 (positive ion mode, [M+H]+, 1 Cl present), m/z=521 (negative ion mode, [M−H]−, 1 Cl present).

Provenance & Evidence