HCID 58833661, compound → HCID 68969604, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-{[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}piperidine-1-carboxylate (0.580 g, 1.13 mmol; prepared in Example 563) was taken up in 4.0 M ethanolic hydrogen chloride (5 mL). The reaction was heated at 65° C. for 1 hour, and then cooled to ambient temperature. The ethanol was removed under reduced pressure and the residue was dissolved in water (3 mL) and saturated aqueous sodium chloride (7 mL). The solution was adjusted to pH 13 with 50% aqueous sodium hydroxide and then extracted with chloroform. The combined organic fractions were sequentially washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated. Trituration with acetonitrile yielded 0.467 g of 1-[4-amino-2-(ethoxymethyl)-7-(piperidin-4-yloxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an off-white solid.

Provenance & Evidence