Trifluoroacetic acid → 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine

Participants

Reaction Steps

A mixture of 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (1.66 g, 4.19 mmol, prepared in Example 34), platinum (IV) oxide (1.5 g, 6.6 mmol), and trifluoroacetic acid (25 mL) was placed in a Parr vessel and shaken under hydrogen pressure (40 psi, 2.8×105 Pa) overnight. The reaction mixture was filtered through a layer of CELITE filter agent, and the filter cake was washed with ethanol. The filtrate was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol). The resulting solid was triturated three times with 10% aqueous sodium hydroxide, isolated by filtration, and washed with water to provide 0.468 g of 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 158-160° C.

Provenance & Evidence