Trifluoroacetic acid → 3-{[{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}(methyl)amino]methyl}-N-{[6-fluoro-3'-(1-piperazinylmethyl)-3-biphenylyl]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}(methyl)amino]methyl}phenyl) carbonyl]amino}methyl)-2′-fluoro-3-biphenylyl]methyl}-1-piperazinecarboxylate (0.055 g, 0.066 mmol) in DCM (0.25 mL) was added TFA (0.25 mL) and stirred at room temperature for 30 min before was diluted with DCM, basified with NaHCO3 (sat. aq.). Organic layer was separated, dried over Na2SO4, filtered, concentrated, purified using a Gilson HPLC (with TFA), final product was basified with an amine cartridge to afford 0.015 g (31%) of the title compound. LC-MS m/z 733 (M+H)+; 1H-NMR (400 MHz, CD3OD) δ ppm 1.24 (t, J=7.40 Hz, 3 H) 1.48 (t, J=7.15 Hz, 3 H) 1.70-1.85 (m, J=10.79 Hz, 2 H) 2.01-2.11 (m, J=12.55, 1.76 Hz, 2 H) 2.56 (s, 3 H) 2.83-2.97 (m, J=7.28 Hz, 2 H) 3.46-3.58 (m, J=5.77 Hz, 8 H) 3.59-3.68 (m, 2 H) 3.92-4.00 (m, J=12.05 Hz, 2 H) 4.01-4.26 (m, J=29.11 Hz, 4 H) 4.26-4.35 (m, 1 H) 4.41-4.50 (m, 4 H) 4.61 (s, 2 H) 7.19 (dd, J=10.67, 8.41 Hz, 1 H) 7.39-7.45 (m, 1 H) 7.50-7.60 (m, 4 H) 7.61-7.70 (m, 2 H) 7.74 (s, 1 H) 7.86 (d, J=8.03 Hz, 1 H) 7.95 (s, 1 H) 8.25 (s, 1 H).

Provenance & Evidence