Acetic Acid → HCID 44193348, compound

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Reaction Steps

A mixture of N-[(6-chloro-3′-formyl-3-biphenylyl)methyl]-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-2,6-pyridinedicarboxamide (50 mg, 0.074 mmol), 1-methylpiperazine (7.36 mg, 0.074 mmol), sodium triacetoxyborohydride (31.2 mg, 0.147 mmol) and acetic acid (5.05 μL, 0.088 mmol) in DCM (1 mL) was stirred at room temperature over the weekend. The reaction mixture was quenched with saturated NaHCO3, and extracted with DCM twice. The combined organic layers were concentrated under vacuum to give a crude residue. It was purified with a Gilson HPLC (with 0.1% TFA in the solvents), eluting with 10 to 70% CH3CN in water at a flow rate of 20 mL/min. The product fractions were combined, converted to the free base with saturated NaHCO3 and the basified solution was extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and then concentrated under vacuum to give N-({6-chloro-3′-[(4-methyl-1-piperazinyl)methyl]-3-biphenylyl}methyl)-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-2,6-pyridinedicarboxamide as a solid (19 mg, 33.8%). LC-MS m/z 765 (M+H)+, 1.44 min (ret time).

Provenance & Evidence