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

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 4-[(3′-{[({4-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]phenyl}carbonyl)-amino]methyl}-3-biphenylyl)methyl]-1-piperazinecarboxylate (0.130 g, 0.16 mmol) in acetonitrile (7.2 mL) and H2O (4800 μL) was added TFA (100 μL, 0.160 mmol). The resultant mixture was applied to a GeneVac EZ-2 evaporator at 45° C. for 8 h. The mixture was further purified using a Gilson HPLC (with 0.1% TFA) and the product-containing fraction concentrated on a GeneVav EZ-2 evaporator at 45° C. for 8 h. The extra TFA was removed by re-dissolving the resultant mixture in DCM and passing it though an amino cartridge. The mixture was concentrated down again by Glas-Col evaporator to afford the title compound 0.0600 g (52%). LC-MS m/z 716 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 1.40 (t, J=7.53 Hz, 3 H) 1.48 (t, J=7.15 Hz, 3 H) 1.81-1.97 (m, 2 H) 2.09 (d, J=12.05 Hz, 2 H) 3.16 (q, J=7.45 Hz, 2 H) 3.56 (s, 8 H) 3.68 (t, J=11.42 Hz, 2 H) 3.99-4.11 (m, J=8.41, 3.14 Hz, 2 H) 4.29-4.41 (m, J=4.27 Hz, 1 H) 4.43-4.53 (m, 4 H) 4.64 (s, 2 H) 4.71 (s, 2 H) 7.35-7.46 (m, 2 H) 7.47-7.61 (m, 3 H) 7.65 (s, 1 H) 7.74 (d, J=7.53 Hz, 1 H) 7.81 (s, 1 H) 7.92-8.03 (m, 4 H) 8.28 (s, 1 H).

Provenance & Evidence