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

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 (1200 mg, 2.344 mmol) in THF (15 ml) was added Et3N (471 mg, 4.668 mmol) followed by 2-methoxyacetyl chloride (254 mg, 2.344 mmol). The reaction was stirred at room temperature for 20 min. After this time, the reaction was diluted with EtOAc (100 ml) and the resulting solution was wash with water (2×50 ml) and saturated NaCl (50 ml). The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified using an ISCO automated chromatography system (120 g silica gel, 20-60% EtOAc/CH2Cl2) to the 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)-2-methoxyacetohydrazide as a light yellow solid 780 mg (57% yield). HPLC retention time 2.858 min (Method A); LCMS (M+H)=583.0.

Provenance & Evidence