Hydrochloric Acid → HCID 11601484, compound

Participants

Reaction Steps

A solution of 2-(ethoxymethyl)-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (prepared as described in Example 5, 0.502 g, 1.68 mmol) in dichloromethane (15 mL) under a nitrogen atmosphere was cooled in an ice bath. A solution of boron tribromide in dichloromethane (1 M, 4.19 mL, 4.19 mmol) was added dropwise. The mixture was allowed to warm slowly to room temperature, then was stirred for 16 hours. The reaction was quenched with methanol (10 mL) and concentrated under reduced pressure to yield a white solid. The solid was treated with 6 M aqueous hydrochloric acid (20 mL) to form a white suspension that was stirred at 50° C. for 2 hours. The mixture was allowed to cool to room temperature and was adjusted to pH 7 with 50% aqueous sodium hydroxide solution. A white solid was isolated by filtration, washed with water, and dried under vacuum. The crude product was purified by chromatography (silica gel, eluted with 1:1 CHCl3:(80:18:2 CHCl3:MeOH:NH4OH)) then was recrystallized from acetonitrile to afford 0.0577 g of [4-amino-1-(isopropylamino)-1H-imidazo[4,5-c]quinolin-2-yl]methanol as white crystals, mp 228–229° C.;

Provenance & Evidence