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

Participants

Reaction Steps

To N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-{[6-fluoro-3′-(hydroxymethyl)-3-biphenylyl]methyl}-1,3-benzenedicarboxamide (0.665 g, 1 mmol) in THF (20 mL) was added MnO2 (0.869 g, 10.00 mmol) and the mixture was stirred at room temperature for 16 h. More MnO2 (10 eq) was added and stirred at room temperature for 4 h and then again for 22 h and then more MnO2 (10 eq) was added. This mixture was stirred at room temperature for 21 h and 94 h then filtered and concentrated to afford the title compound (0.6472 g, 98%). LC-MS m/z 663 (M+H)+.

Provenance & Evidence