Chloroacetyl chloride → 2-chloro-N'-(4-(4-chlorophenyl)-5-(4-cyanophenyl)-1-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-1,6-dihydropyridazin-3-yl)acetohydrazide

Participants

Reaction Steps

To a solution of 4-(5-(4-chlorophenyl)-6-hydrazinyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile (500 mg, 0.977 mmol) in THF (7 ml), Et3N (197 mg, 1.953 mmol) was added chloroacetyl chloride (110 mg, 0.977 mmol). The reaction was stirred at room temperature for 30 min. The reaction mixture was diluted with EtOAc (50 ml) and the resulting solution was washed with water (2×20 ml) and saturated NaCl (20 ml). The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified using an ISCO automated chromatography system (12 g silica gel, 20-40% EtOAc/CH2Cl2) to give the product 2-chloro-N′-(4-(4-chlorophenyl)-5-(4-cyanophenyl)-1-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-1,6-dihydropyridazin-3-yl)acetohydrazide as a light yellow solid (410 mg, 72% yield). HPLC retention time 2.920 min (Method A); LCMS (M+H)=587.0.

Provenance & Evidence