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

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 4-[(5′-{[({3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-phenyl}methyl)(methyl)amino]-methyl}-2′-fluoro-3-biphenylyl)methyl]-1-piperazinecarboxylate (0.386 g, 0.463 mmol) in DCM (3.6 mL) was added TFA (1.8 mL) and this mixture was stirred at room temperature for 100 min before being quenched with NaHCO3 (sat. aq.). This mixture was extracted with DCM, concentrated, purified using a Gilson HPLC (with TFA). Product was basified with an amine cartridge to afford 0.068 g (20%) of the title compound. LC-MS m/z 733 (M+H)+; 1H-NMR (400 MHz, CD3OD) δ ppm 1.40 (t, J=7.65 Hz, 3 H) 1.49 (t, J=7.15 Hz, 3 H) 1.79-1.92 (m, 2 H) 2.05-2.14 (m, 2 H) 2.74 (s, 3 H) 3.18 (q, J=7.61 Hz, 2 H) 3.43-3.58 (m, 8 H) 3.63-3.72 (m, 2 H) 3.99-4.07 (m, 2 H) 4.30-4.62 (m, 9 H) 4.72 (s, 2 H) 7.34 (dd, J=10.42, 8.66 Hz, 1 H) 7.54-7.65 (m, 4 H) 7.67-7.78 (m, 4 H) 8.02 (d, J=8.03 Hz, 1 H) 8.12 (s, 1 H) 8.29 (s, 1 H).

Provenance & Evidence