1,3-Cyclohexanedione → HCID 59825760, compound

Participants

Reaction Steps

A suspension of 154.2 mg (1.0 mmol) of 3-amino-2-ethoxycarbonylpyrrole and 245.3 mg (1.0 mmol) of 5-(3H-imidazo[4,5-c]pyridin-2-ylsulfanyl)-furan-2-carbaldehyde (obtained from step 1) in 10 mL of n-butanol under argon is stirred at room temperature for 15 min. 1,3-Cyclohexanedione (112.1 mg, 1.0 mmol) is then added and the reaction mixture is heated at reflux temperature for 2 h. The mixture is then cooled to room temperature and concentrated under reduced pressure. The residue is triturated in ethanol, filtered and washed with diethyl ether. The solid is purified by chromatography on a prepacked 70 g 15-40 μm silica gel cartridge (eluting solvent: dichloromethane/methanol from 100/0 to 80/20 v/v; rate: 40 mL/min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. 178 mg of 9-[5-(3H-imidazo[4,5-c]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 beige powder. LCMS: m/z 476: [M+H]+ (base peak). Anal. Calcd for C24H21N5O4S: C, 60.62; H, 4.45; N, 14.73; O, 13.46; S, 6.74. Found: C, 59.41; H, 4.47; N, 14.33; S, 6.41; H2O, 2.11%.

Provenance & Evidence