Methanol → 3,3-dimethoxy-1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutanamine

Participants

Reaction Conditions

Reaction Steps

To a micro reactor vessel was added (2-(1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-3-oxocyclobutyl)-1H-isoindole-1,3(2H)-dione (1-13) (100 mg, 0.162 mmol), TFA (1 mL), and MeOH (5 mL), and the mixture was heated under microwave irradiation at 100° C. for 10 minutes. Then hydrazine hydrate (80 mg, 1.6 mmol) was added, and the mixture was heated under microwave irradiation at 100° C. for 10 minutes. The solvent was concentrated under reduced pressure, and the residue was purified by reverse phase column chromatography (Sunfire C18) eluting with 5 to 95% acetonitrile/(0.1% TFA/water) gradient. The appropriate fractions were free based by suspending in ethyl acetate, washed with a saturated solution of sodium bicarbonate, followed by water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 3,3-dimethoxy-1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutanamine (1-18). HRMS (M+H)+: observed=532.2461, calculated=532.2466.

Provenance & Evidence