3-chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile → HCID 178509927, Verbindung

Beteiligte Stoffe

Reaktionsschritte

3-chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile (135 mg, 0.195 mmol) was dissolved in TFA (10 mL) and placed in an oil bath at 75° C. After 2 hours, the reaction was allowed to cool to room temperature and was concentrated under reduced pressure. The resulting residue was diluted with CHCl3/EtOAc (4:1, 50 mL) and methanol was added until a solution was achieved. 50% Aqueous sodium bicarbonate (10 mL) was then added. The organic phase was removed and the aqueous was extracted with CHCl3 (25 mL). The combined organic fractions were, dried (MgSO4), filtered and concentrated. The resulting residue was adsorbed onto silica gel with CHCl3/MeOH and purified by automated column chromatography on silica gel (12 g), eluting with 0-5% MeOH/CH2Cl2 to afford the title compound. 1H NMR (DMSO d-6) δ 7.82 (d, J=9.0 Hz, 1H), 7.81 (m, 1H), 7.75 (d, J=9.0 Hz, 1H), 7.58 (m, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.52 (m, 1H), 6.36 (m, 1H), 6.30 (d, J=8.8 Hz, 1H), 6.16 (s, 1H).

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