Tert-butyl 3-(4-{[(1-adamantylmethyl)amino]-carbonyl}-5-chloropyridin-2-yl)prop-2-ynyl(ethyl)carbamate → N-(1-Adamantylmethyl)-5-chloro-2-[3-(ethylamino)propyl]isonicotinamide hydrochloride

Participants

Reaction Steps

The titled compound was prepared from tert-butyl 3-(4-{[(1-adamantylmethyl)amino]-carbonyl}-5-chloropyridin-2-yl)prop-2-ynyl(ethyl)carbamate (Example 7(ii)) (0.30 g) by the method of Example 6(ii). The crude hydrochloride salt was suspended in 2M aqueous sodium hydroxide solution (25 ml), extracted into ethyl acetate (3×25 ml). and the combined extracts were concentrated. The residue was purified by chromatography on silica gel eluting with dichloromethane:methanol:0.88 aqueous ammonia (89:10:1). The isolated material was dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml of a 4M solution) and concentrated; the resultant solid was triturated with ethyl acetate and the solid collected by filtration. Final purification was by preparative reverse phase HPLC to afford the titled compound (0.025 g) as a colourless powder.

Provenance & Evidence