m-Chloroperbenzoic acid → HCID 69506693, compound

Participants

Reaction Steps

A modification of the methods described in Part B of Example 60 was used to treat ethyl 3-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate (11.0 g, 31 mmol) with mCPBA (13.6 g of 77% pure material), followed by trichloroacetyl isocyanate (4.4 mL, 37 mmol). The reaction with the isocyanate was stirred for 1.5 hours before the addition of additional trichloroacetyl isocyanate (4.4 mL) and stirring for three days. Additional trichloroacetyl isocyanate (0.5 mL) was added, and the reaction was stirred for four hours. After the addition of methanol (50 mL), the solution was stirred overnight, and then the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (150 mL), and the solution was washed with saturated aqueous sodium bicarbonate (2×35 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 5% methanol in dichloromethane containing 2 mL ammonium hydroxide per liter of eluent) to provide 11.4 g of methyl 3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate as a semi-solid.

Provenance & Evidence