Trifluoroacetic acid → N-({3'-[(1S,4S)-2,5-Diazabicyclo [2.2.1]hept-2-ylmethyl]-6-fluoro-3-biphenylyl}methyl)-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide

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Reaction Steps

1,1-Dimethylethyl (1S,4S)-5-[(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]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.0488 g, 0.058 mmol) was dissolved in CH2Cl2 (9 mL) and treated with trifluoroacetic acid (1 mL) at 0° C. and then allowed to warm to room temperature. This mixture was stirred for a total of 2 h. The solvents were pumped off, and the material was passed though 2 quaternary ammonium hydroxide cartridges, but 19F NMR still indicated residual TFA. The product was taken up in EtOAc and washed 3× with 0.5 N NaOH, 1× with brine, dried over anhydrous Na2SO4, filtered, and concentrated to give the title compound as a tan solid. LC-MS m/z 746 (M+H)+, 1.30 min (ret time); mp 129-133° C. Analytical HPLC shows 96.8% purity, (ret time 9.820 min).

Provenance & Evidence