4-Toluenesulfonyl chloride → 3-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-1-ol

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Reaction Steps

p-Toluenesulphonyl chloride (0.93 g) was added portionwise to a vigourously stirred mixture of the product from step (iv) (1.77 g) in DCM (50 mL) and ammonium hydroxide solution (35%, 5 mL) at rt. The reaction mixture was stirred for 3 h then partitioned between water/DCM. The organics were washed with saturated NaHCO3 solution, water, dried, and the solvent evaporated under reduced pressure. The residue was dissolved in MeOH (40 mL), water (20 mL) then 6M NaOH solution (2 mL) added and the mixture stirred at rt for 18 h. The solid formed was filtered off washed with water and dried, yield 965 mg.

Provenance & Evidence