1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67129301, compound

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 (70 mg, 0.1367 mmol), N-Boc-alanine (24 mg, 0.1367 mmol), EDAC (30 mg, 0.150 mmol), HOBT (20.3 mg, 0.150 mmol) THF (5 ml) and diisopropyl ethyl amine (0.026 ml, 0.150 mmol). The reaction was stirred at rt for 5 hr. After this time the reaction mixture was diluted with EtOAc (25 ml). The resulting solution was washed with water (2×15 ml) and saturated NaCl (15 ml). The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel column chromatography (8 g silica gel) eluting with a gradient of 20%-100% EtOAc/Hex to give product tert-butyl 2-(2-(4-(4-chlorophenyl)-5-(4-cyanophenyl)-1-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-1,6-dihydropyridazin-3-yl)hydrazinyl)-2-oxoethylcarbamate as a light yellow solid (54 mg, 60% yield)

Provenance & Evidence