Hydrochloric Acid → (S)-2-(4-(2-amino-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)-N-(3,4-dimethoxyphenyl)benzo[d]thiazole-6-carboxamide hydrochloride

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Reaction Steps

(S)-tert-butyl 1-(4-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate (0.95 g, 1.45 mmol) was dissolved in 1,4-dioxane (2 ml) and treated with 4M HCl in 1,4-dioxane (2 ml). The resulting mixture was stirred at room temperature overnight. The resulting solid was filtered and treated with 4M HCl in 1,4-dioxane (2 ml), again stirring overnight. The solid was filtered, dissolved in dichloromethane and washed with saturated NaHCO3 to yield the title compound as its corresponding free base. The free base was chromatographed eluting with dichloromethane/methanol/ammonium hydroxide to yield the free base as a residue. The free base residue (0.50 g, 0.91 mmol) was dissolved in dichloromethane (2 ml) and treated with 1M HCl in diethyl ether (0.91 ml, 0.91 mmol) and the resulting mixture stirred at room temperature for 2 h. The resulting solid was filtered, washed with diethyl ether (2×) and dried to yield (S)-2-(4-(2-amino-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)-N-(3,4-dimethoxyphenyl)benzo[d]thiazole-6-carboxamide, as its corresponding hydrochloride salt.

Provenance & Evidence