1,3-Cyclohexanedione → HCID 178515825, compound

Participants

Reaction Steps

A mixture of 3-aminopyrazole (0.089 g, 1.07 mmol), 5-(4,6-difluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (described in example 142, 0.30 g, 1.07 mmol) and 1,3-cyclohexanedione (0.12 g, 1.07 mmol) in 5 ml of 1-butanol is heated at reflux temperature for 3 hours. The reaction mixture is then concentrated under reduced pressure and the residue is purified on a silica gel column (40 g) eluted with a mixture of cyclohexane and ethyl acetate (2/8, v/v). The fractions containing the expected product are concentrated under reduced pressure and the obtained solid is washed with pentane (25 ml) and diisopropylether (25 ml) and dried under vacuum to yield 323 mg of 4-[5-(5,7-difluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-2,4,6,7,8,9-hexahydro-pyrazolo[3,4-b]quinolin-5-one as a white powder. Yield=69%. Analytical LC/MS (method C): m/z=438 (negative ion mode [M−H]−), m/z=440 (positive ion mode [M+H]+)

Provenance & Evidence