Toluene → 7-benzyloxy-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

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Reaction Steps

The preparation of 7-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine is described in Parts A-F of Example 1. A concentrated solution of ethoxyacetyl chloride (12.2 g, 99.2 mmol) was added dropwise to a solution of 7-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine (29 g, 90 mmol) in 50:50 toluene:pyridine. The temperature of the reaction reached 40° C., and a precipitate formed. Triethylamine (15-20 g) and pyridine were added to help dissolve the precipitate. The reaction was heated at reflux for three hours and then allowed to cool to ambient temperature overnight. The solvents were removed under reduced pressure, and the black residue was dissolved in dichloromethane. The resulting solution was washed several times with aqueous sodium carbonate (150 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 29.2 g of 7-benzyloxy-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline as a tan solid.

Provenance & Evidence