Trifluoroacetic acid → HCID 59177899, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added 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 (54 mg, 0.0808 mmol), acetonitrile (3 ml), and tetra-chloro-1,2-dibromo-ethane (58 mg, 0.178 mmol). The reaction was cooled to 0° C. Triphenylphosphine (47 mg, 0.178 mmol) was then added and the reaction was stirred at 0° C. for 5 min. After this time, Et3N (0.05 ml, 0.356 mmol) was added to the reaction. The reaction was slowly warmed up to rt and stirred for 16 hrs. After this time, the reaction was diluted with EtOAc (25 ml). The resulting solution was washed with water (2×20 ml) and saturated NaCl (20 ml). The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel column chromatography (8 gm silica gel) eluting with a gradient of 20%-80% EtOAc/Hex to give the cyclized intermediate. This material was then dissolved in CH2Cl2(1 ml) and TFA (1 ml) was added. The reaction was stirred at rt for 1 hr. After this time, the solvent was removed. The residue was diluted with EtOAc (20 ml). The resulting solution was washed with saturated NaHCO3(20 ml), water (10 ml) and saturated NaCl (10 ml). The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel column chromatography (4 g silica gel) eluting with a gradient of 100% EtOAc and then 5% MeOH/CH2Cl2 to give product as a white solid (15 mg, 34% yield).

Provenance & Evidence