Triethylamine → HCID 59130427, compound

Participants

Reaction Steps

Triethylamine (1.86 mL, 13.4 mmol) was added to a mixture of 1-[3-(aminooxy)propyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 6.68 mmol), prepared as described in Example 1, and chloroform (20 mL). Cyclopropanecarbonyl chloride (673 microliters (μL), 7.35 mmol) was then added, and the resulting solution was stirred at room temperature overnight. The reaction was diluted with chloroform (50 mL), washed with brine (2×100 mL) and saturated aqueous sodium bicarbonate (2×100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified twice by column chromatography on silica gel (eluting sequentially with 97:2:1-dichloromethane:methanol:ammonium hydroxide and 96:3:1-dichloromethane:methanol:ammonium hydroxide) to provide 532 milligrams (mg) of N-[3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propoxy]cyclopropanecarboxamide as a white powder, mp 103-105° C.

Provenance & Evidence