Trifluoroacetic acid → HCID 11630397, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (150 mL) was added to N4,N4-bis(4-methoxybenzyl)-N2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine (15 g, 29.5 mmol), and the reaction was heated at 70° C. overnight and allowed to cool to ambient temperature. Aqueous sodium hydroxide (170 mL of 12 M) was added to adjust the solution to pH 9. The resulting mixture was extracted with chloroform (3×), and the combined extracts were washed with brine (3×), dried over magnesium sulfate, filtered through a layer of CELITE filter agent, and concentrated under reduced pressure. The residue was purified by automated flash chromagraphy (silica cartridge, eluting with 0-25% methanol in ethyl acetate). The resulting product was further purified twice by flash chromatography on silica gel (eluting first with 5-10% methanol in dichloromethane and then 5-7.5% methanol in dichloromethane) to provide 3 g of N2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine.

Provenance & Evidence