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

Participants

Reaction Steps

To a round bottom flask was added 5-(4-chlorophenyl)-6-hydrazinyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-4-(pyridin-4-yl)pyridazin-3(2H)-one (200 mg, 0.41 mmol), THF (5 ml), Et3N (124 mg, 1.232 mmol) followed by propionyl chloride (57 mg, 0.616 mmol). The reaction was then stirred at rt for 20 min. The reaction mixture was diluted with EtOAc (30 ml). The resulting solution was wash 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, 12 gm silica gel) eluting with 100% EtOAc for 10 min, then 5% MeOH in CH2Cl2 to give product N′-(4-(4-chlorophenyl)-1-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-5-(pyridin-4-yl)-1,6-dihydropyridazin-3-yl)propionohydrazide as light yellow solid 140 mg(63% yield). HPLC retention time (method A)1.892 min; LCMS (M+1)=543.3.

Provenance & Evidence