1,3-Cyclohexanedione → HCID 178470347, compound

Participants

Reaction Steps

A mixture of 3-amino-2-ethoxycarbonyl-pyrrole (0.158 g, 1.02 mmol), 5-(5-chloro-7-methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (0.30 g, 1.02 mmol) and 1,3-cyclohexanedione (0.115 g, 1.02 mmol) in 5 ml of 1-butanol is heated at reflux temperature for 4 h. The reaction mixture is then concentrated under reduced pressure and the residue is 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 triturated in diisopropylether and pentane. The obtained solid is then resuspended in 5 ml acetonitrile, heated at reflux temperature for 30 minutes and let to cool to room temperature. The insoluble material is collected by filtration and dried under vacuum to deliver 100 mg of 9-[5-(5-chloro-7-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=20%. 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