1,3-Cyclohexanedione → HCID 178470348, compound

Participants

Reaction Steps

A suspension of 69.2 mg (0.45 mmol) of 3-amino-2-ethoxycarbonylpyrrole and 110.0 mg (0.45 mmol) of 5-(1H-imidazo[4,5-b]pyridin-2-ylsulfanyl)-furan-2-carbaldehyde (obtained from step 1) in 5 mL of ethanol under argon is stirred at room temperature for 1 hour. 1,3-Cyclohexanedione (50.3 mg, 0.45 mmol) is then added and the reaction mixture is heated at reflux temperature for 16 h. The mixture is then cooled to room temperature and concentrated under reduced pressure. The residue is purified by chromatography on a prepacked 30 g 15-40 μm silica gel cartridge (eluting solvent: dichloromethane/methanol from 100/0 to 90/10 v/v). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. The residue is purified by chromatography on a prepacked 30 g 15-40 μm silica gel cartridge (eluting solvent: toluene/2-propanol 85/15 v/v). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. The residue is purified by chromatography on a prepacked 25 g 15-40 μm silica gel cartridge (eluting solvent: toluene/2-propanol 85/15 v/v). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. The residue is purified by chromatography on a prepacked 15 g 15-40 μm silica gel cartridge (eluting solvent: ethyl acetate/methanol/triethylamine 92/4/4 v/v/v). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. 37 mg of 9-[5-(3H-imidazo[4,5-b]pyridin-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 are obtained as a yellow powder. mp: 190-202° C. LCMS: m/z 476: [M+H]+ (base peak); m/z 474: [M−H]− (base peak).

Provenance & Evidence