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

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Reaction Steps

(S)-2-(4-(2-(tert-Butoxycarbonylamino)-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (0.084 g, 0.155 mmol), cyclopentylamine (0.015 ml, 0.155 mmol), diisopropylethylamine (0.11 ml, 0.62 mmol) and HBTU (0.076 g, 0.20 mmol) were dissolved in DMF (4 ml) and the resulting mixture stirred overnight. The resulting mixture was then diluted with ethyl acetate (9 ml), washed with 1N HCl (3×5 ml), brine (5 ml), dried (MgSO4) and concentrated in vacuo. The resulting residue was chromatographed eluting with dichloromethane/methanol (97:2) to yield a residue which was dissolved in 1,4-dioxane (1 ml) and treated with 4M HCl in 1,4-dioxane for three days. The resulting solid was filtered, washed with ether (3×) and dried to yield (S)-2-(4-(2-amino-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)-N-cyclopentylbenzo[d]thiazole-6-carboxamide (Compound #26).

Provenance & Evidence