1,2-Dimethoxyethane → N-(6-Fluoro-2-Methyl-3-{5-[(5-Methyl-4,5,6,7-Tetrahydropyrazolo[1,5-A]pyrazin-2-Yl)amino]-6-Oxo-1,6-Dihydropyridazin-3-Yl}phenyl)-1-Benzothiophene-2-Carboxamide

Participants

Reaction Steps

A microwave tube equipped with a magnetic stirrer was charged with 6-chloro-4-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridazin-3(2H)-one (225 mg, 0.80 mmol), N-(6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[b]thiophene-2-carboxamide (463 mg, 1.13 mmol), DME (5 mL) and 1M aqueous sodium carbonate (2 mL). After bubbling Argon while sonicating for 30 sec, Pd(PPh3)4 (65 mg, 0.06 mmol) was added. The mixture was subjected to microwave irradiation at 150° C. for 20 min. After this time, ethyl acetate (10 mL) and water (10 mL) were added. The separated aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organics were washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford the title compound N-{6-fluoro-2-methyl-3-[5-({5-methyl-4H,5H,6H,7H-pyrazolo[1,5-a]pyrazin-2-yl}amino)-6-oxo-1,6-dihydropyridazin-3-yl]phenyl}-1-benzothiophene-2-carboxamide (211 mg) in 50% yield.

Provenance & Evidence