Hydrochloric Acid → N-(1-benzyl-4,6-dichloro-1H-indol-2-ylmethyl)-N'-(4-methoxyquinolin-2-yl)propane-1,3-diamine

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Reaction Steps

A solution of 1-benzyl-4,6-dichloro-1H-indole-2-carboxylic acid [3-(4-methoxy-quinolin-2-ylamino)-propyl]-amide (200 mg, 0.37 mmol) [from example 12] in anhydrous tetrahydrofuran (15 ml) was treated with 1 N borane-tetrahydrofuran complex (1.1 ml, 1.1 mmol). The solution was heated a reflux for 24 hours then cooled to ambient temperature. Treated with the dropwise addition of concentrated hydrochloric acid (1 ml) then stirred for 1 hour. Evaporated under reduced pressure to a residue and taken into a system of saturated aqueous sodium chloride (20 ml) and 10% sodium hydroxide (20 ml). Extracted into ethyl acetate. The extracts were dried (sodium sulfate) then evaporated to an oil. Column chromatography on silica (95/5 methylene chloride/methanolic ammonia) gave N-(1-benzyl-4,6-dichloro-1H-indol-2-ylmethyl)-N′-(4-methoxyquinolin-2-yl)propane-1,3-diamine as a colorless resin. This was taken into chloroform (5 ml) then treated with 4N hydrogen chloride in 1,4-dioxane (300 μl). Evaporation under reduced pressure gave N-(1-benzyl-4,6-dichloro-1H-indol-2-ylmethyl)-N′-(4-methoxyquinolin-2-yl)propane-1,3-diamine dihydrochloride (102 mg, 42%) as a white solid. [M+H]+ 519.

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