HCID 10990514, compound → HCID 21833021, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 4-(2-dimethylaminoethyl)-2,3,6,7,8,9-hexahydro-4H-pyrido[2,3-g][1,4]benzoxazine (D5, 130 mg, 0.49 mmole) in toluene (4 ml) under argon was treated with trimethylaluminium (0.27 ml of 2M in toluene, 0.54 mmole) and stirred for 20 mins. Methyl 2'-methyl4'-(2-oxo-1-pyrrolidinyl)biphenyl-4-carboxylate (D29, 154 mg, 0.50 mmole) was added and the mixture heated at 80-85° C. for 6 h, then further trimethylaluminium (0.45 ml) was added and the mixture heated under reflux for 6 h. The reaction mixture was allowed to cool, poured into a slurry of silica gel (4 g) in dichioromethane (10 ml), then loaded onto a chromatography column and eluted with 0-16% methanol/dichloromethane. The product obtained was further purified by prep. plate TLC on silica gel eluting with 10% methanol/dichloromethane to afford the title compound as a light green semi-solid (16 mg). This was converted to it hydrochloride salt as a pale yellow solid.

Provenance & Evidence