Diisopropylethylamine → 5-[1-(3-Fluoro-5-trifluoromethyl-benzyl)-piperidin-4-ylamino]-[1,3,4]thiadiazole-2-carbonitrile

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Reaction Steps

A mixture of 5-(piperidin-4-ylamino)-[1,3,4]thiadiazole-2-carbonitrile (D6) (0.16 g, 0.76 mmol), 3-fluoro-5-(trifluoromethyl)benzyl bromide (0.124 ml, 0.76 mmol) and diisopropylethylamine (0.20 ml, 1.14 mmol) in acetonitrile (2 ml) and N,N-dimethylformamide (0.5 ml) was stirred at room temperature for 48 h. After this period, the reaction mixture was diluted with dichloromethane and extracted with a saturated solution of ammonium chloride (25 ml). The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 2-3% ammonia in methanol (7M)/dichloromethane) to yield E18 (0.019 g, 7%) as a solid. C16H15F4N5S requires 385. Found 386 (MH+).

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