Trifluoroacetic acid → HCID 57550526, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (20 mL) was added to N2-ethyl-N4,N4-bis(4-methoxybenzyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine (2.0 g, 3.8 mmol), and the reaction was heated at 50° C. for four hours and allowed to cool to ambient temperature. Aqueous sodium hydroxide (6 M) was added to adjust the solution to pH 9, and then dichloromethane and saturated aqueous sodium bicarbonate were added. The organic layer was separated and washed twice with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered through a layer of CELITE filter agent, and concentrated under reduced pressure. The residue was purified twice by automated flash chromatography (silica cartridge, eluting with 12% methanol in dichloromethane followed by silica cartridge, eluting with 3-12% methanol in dichloromethane). The resulting product was recrystallized from acetonitrile containing a few drops of methanol, combined with material from another run, and recrystallized again using the same solvents to provide 210 mg of N2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine as beige needles, mp 188-190° C.

Provenance & Evidence