Sodium hydride → 2-[benzothiazol-2(3H)-ylidene]-2-[5-(4-methylpiperazine-1-carbonyl)-4-trifluoromethylpyrimidin-2-yl]acetamide hydrochloride

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Reaction Steps

Sodium hydride 99% (50.8 mg, 2.1 mmol) was added to a suspension of 2-(benzothiazol-2-yl)acetamide (103 mg, 0.53 mmol) in THF (2 mL), and the resulting yellow suspension was stirred at room temperature for 15 min. The mixture was cooled to 0° C. and (2-chloro-4-trifluoromethyl-pyrimidin-5-yl)(4-methylpiperazin-1-yl)methanone (0.18 g, 0.53 mmol) was added. The mixture was stirred at room temperature overnight and the solvent was then removed under reduced pressure. The residue was suspended in water and the pH adjusted to 7 with 1N hydrochloric acid. The solid was collected by filtration and partitioned between EA and water. The EA phase was separated, washed with brine, dried over magnesium sulfate, and concentrated under vacuum. The resulting material was purified by reverse phase preparative HPLC to give 2-[benzothiazol-2(3H)-ylidene]-2-[5-(4-methylpiperazine-1-carbonyl)-4-trifluoromethylpyrimidin-2-yl]acetamide hydrochloride (87 mg, 33% yield) as a yellow solid.

Provenance & Evidence