4-Toluenesulfonyl chloride → HCID 86596851, compound

Participants

Reaction Steps

A solution of tert-butyl {3-[(2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}carbamate (1.39 g, 3.35 mmol) in 35 mL of CHCl3 was treated with 15 mL of concentrated NH4OH solution and p-toluenesulfonyl chloride (0.67 g, 3.51 mmol). After 15 min, the reaction mixture was diluted with water and CHCl3 and the phases were separated. The organic portion was washed with 10% Na2CO3 solution and water. The combined aqueous washes were back-extracted with CHCl3. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield tert-butyl {3-[(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}carbamate (1.30 g) as an orange foam.

Provenance & Evidence