Dimethylacetamide → 4-{3-[4-(4-Carbamoyl-benzo[b]thiophen-2-yl)-5-chloro-pyrimidin-2-ylamino]-propyl}-piperazine-1-carboxylic acid tert-butyl ester

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Reaction Steps

4-(3-Aminopropyl)-piperidine-1-carboxylic acid tert-butyl ester (0.818 g, 3.36 mmol) is added to a stirred suspension of 2-(2,5-dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid amide (0.436 g, 1.34 mmol) and diisopropylethylamine (0.70 mL, 4.0 mmol) in anhydrous 1,4-dioxane (8 mL) and dimethylacetamide (2 mL) at room temperature under nitrogen. The resultant mixture is heated in an oil bath at 95° C. for 7 hours. At room temperature the mixture is concentrated and chromatographed on silica gel, eluting with CH3OH in dichloromethane: 0-6%, to give 4-{3-[4-(4-carbamoyl-benzo[b]thiophen-2-yl)-5-chloro-pyrimidin-2-ylamino]-propyl}-piperazine-1-carboxylic acid tert-butyl ester (0.403 g) as a solid.

Provenance & Evidence