Diisopropylethylamine → HCID 67005943, compound

Participants

Reaction Steps

205(a) 3-{[({3′-[((3S)-4-{[(1,1-Dimethylethyl)oxy]carbonyl}-3-methyl-1-piperazinyl)methyl]-6-fluoro-3-biphenylyl}methyl)amino]carbonyl}benzoic acid (1150 mg, 2.0 mmol) was dissolved in dichloromethane (DCM) (100 mL), and then HBTU (830 mg, 2.2 mmol), 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (620 mg, 2.0 mmol), and DIPEA (1.4 mL, 8.0 mmol) were added. The mixture was allowed to stir under argon at room temperature overnight. Solvents were concentrated and then purified on a 40 g Redi-Sep cartridge and eluting with 0.5% MeOH in DCM. Collected clean fractions were combined solvent concentrated to give 1,1-dimethylethyl (2S)-4-[(5′-{[({3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]phenyl}carbonyl)amino]methyl}-2′-fluoro-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate (1.15 g, 66.5%) as a white solid.

Provenance & Evidence