Tetrahydrofuran → N'-(4-(4-chlorophenyl)-5-(4-cyanophenyl)-1-((2-methyl-6-(trifluoromethyl)pyridin-3-yl) methyl)-6-oxo-1,6-dihydropyridazin-3-yl)propionohydrazide

Participants

Reaction Steps

To a round bottom flask was added 4-(5-(4-chlorophenyl)-6-hydrazinyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile (96 mg, 0.187 mmol), THF (31 ml), Et3N (37.8 mg, 0.374 mmol) and propionyl chloride (17.3 mg, 0.187 mmol). The resulting reaction mixture was stirred at rt for 20 min. After this time, the reaction mixture was diluted with EtOAc (30 ml). The resulting solution was poured into a separatory funnel and the layers were separated. The organic layer was washed with water (2×10 ml) and saturated aqueous NaCl (10 mL). The organic layer was then slurried with MgSO4 to remove excess water, filtered and concentrated to give the crude product. The crude product was purified using an automated column chromatography system (ISCO, 4 gm silica gel) eluting with a gradient of 20-80% EtOAc/Hex to give product N′-(4-(4-chlorophenyl)-5-(4-cyanophenyl)-1-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-1,6-dihydropyridazin-3-yl)propionohydrazide as light yellow solid 50 mg (47% yield, for 2 steps). HPLC retention time (method A) 2.941 min; LCMS (M+H)=567.3.

Provenance & Evidence