2,6-Dimethylpiperazine → N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-({3'-[(3,5-dimethyl-1-piperazinyl)methyl]-6-fluoro-3-biphenylyl}methyl)pentanediamide

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Reaction Steps

N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-[(6-fluoro-3′-formyl-3-biphenylyl)methyl]pentanediamide (47.0 mg, 0.076 mmol) was diluted in DMSO (1.0 mL) and dispensed into a 1 dram vial containing 2,6-dimethylpiperazine (0.76 mmol), ZnCl2 (0.032 mmol, 4.2 mg), NaB(OAc)3H (0.76 mmol, 180 mg) and fitted with a magnetic stir bar, for 12 h. The material was purified via reverse phase HPLC using a Gilson and the desired product collected. The desired product was dissolved in dichloromethane (1 mL) and washed through 2 g SPE-amine columns (EtOAc:MeOH=4:1, 5 mL) to afford the title compound. LC-MS m/z 727 (M+H)+, 1.09 min (ret time).

Provenance & Evidence