1,3-Cyclohexanedione → HCID 178470346, compound

Participants

Reaction Steps

A mixture of 3-amino-2-ethoxycarbonyl-pyrrole (0.276 g 1.79 mmol), 5-(6-chloro-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (0.5 g, 1.79 mmol) and 1,3-cyclohexanedione (0.201 g, 1.79 mmol) in 5 ml of ethanol is heated at reflux temperature for 2 hours. The reaction mixture is then concentrated under reduced pressure and 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 concentrated under reduced pressure and then purified using preparative LC/MS method B on a Xbridge C18 column (Waters, 30*100 mm) eluted with a 0 to 50% gradient of acetonitrile in aqueous 10 mM ammonium formate pH=9.0 at a 30 ml/min. flow rate in 12 min. The fraction containing the expected product are concentrated under reduced pressure. The residue is resuspended in 2 ml of acetonitrile, heated at reflux temperature and cold to room temperature. The insoluble material is collected by filtration, washed with diisopropyl ether (2×2 ml) and dried under vacuum to yield 115 mg of 9-[5-(5-chloro-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=12%. Analytical LC/MS (method B): m/z=509 (positive ion mode, [M+H]+, 1 Cl present), m/z=507 (negative ion mode, [M−H]−, 1 Cl present)

Provenance & Evidence