Hydrochloric Acid → N-[4-(4-amino-2-ethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide

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Reaction Steps

A warm solution of N-[4-(4-amino-7-benzyloxy-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide (2.00 g, 4.28 mmol), prepared in Example 106, in acetonitrile (250 mL) and methanol (50 mL) was added to a Parr vessel containing 10% palladium on carbon (1.00 g) and a small amount of acetonitrile. The vessel was placed under hydrogen pressure (25 psi, 1.7×105 Pa) and recharged three times with hydrogen over a period of 21 hours. Concentrated hydrochloric acid (30 mL) was then added to the reaction mixture, which was filtered through a layer of CELITE filter aid. The filter cake was washed with water (200 mL), and the filtrate was concentrated under reduced pressure. Ethanol (2×100 mL) was added to the residue and concentrated under reduced pressure to afford a white solid. The solid was mixed with water (30 mL), and the pH was adjusted to 8 with the addition of 1M aqueous sodium hydroxide. The resulting white, granular precipitate was isolated by filtration, washed with water and ethanol, stirred with hot ethanol, and isolated by filtration to provide 0.860 g of N-[4-(4-amino-2-ethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide as a white powder, mp 220° C. (decomposition).

Provenance & Evidence