Benzene → HCID 52934731, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 ml flask a mixture of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-quinolinecarboxamide (for a preparation see Intermediate 56, 331 mg) and (2-pyrimidinylmethyl)amine (273 mg) in acetonitrile was heated at 100° C. for 2 h. The reaction mixture was hydrolyzed with a solution of sodium hydrogen carbonate, extracted with DCM and the organic dried over Na2SO4, filtered and concentrated to dryness to give 350 mg of crude intermediate. The residue was dissolved in acetonitrile (15 ml), bis(trifluoroacetoxy)iodo]benzene (0.5 g) was added and the reaction mixture was stirred for 3 h at room temperature. The reaction mixture was washed with water, extracted with DCM and the organic dried over Na2SO4, filtered and concentrated to dryness. The resulting crude compound was purified by chromatography on silica gel eluting with DCM/methanol (95:5) and the resulting residue was recrystallised from acetonitrile and dried in vacuo to give 7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1-(2-pyrimidinylmethyl)-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one (70 mg) as a beige powder.

Provenance & Evidence