1,3-Cyclohexanedione → HCID 178470353, compound

Participants

Reaction Steps

A mixture of 3-amino-2-ethoxycarbonyl-pyrrole (0.248 g, 1.61 mmol), 5-(6-difluoromethoxy-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (0.5 g, 1.61 mmol) and 1,3-cyclohexanedione (0.181 g 1.61 mmol) in 5 ml of ethanol is heated at reflux temperature for 2 hours. The reaction mixture is then concentrated under reduced pressure and dissolved in 5 ml of ethyl acetate. The organic phase is washed twice with 2 ml of water, dried over MgSO4 and concentrated under reduced pressure. The residue is purified on a silica gel column (120 g) eluted with a mixture of dichloromethane and methanol (99/1, v/v). The fractions containing the expected products are pooled and concentrated under reduced pressure. The residue is resuspended in 20 ml of acetonitrile, the mixture is heated at reflux temperature for 15 minutes and then let to cool to room temperature. The insoluble material is collected by filtration and dried under vacuum for 1 hour at 30° C. to yield 203 mg of 9-[5-(5-difluoromethoxy-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 as a white powder. Yield=23%. Analytical LC/MS method B: m/z=541 (positive ion mode [M+H]+), m/z=539 (negative ion mode [M−H]−)

Provenance & Evidence