[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[C:13]([C:17]([CH3:29])([CH2:27][CH3:28])[CH2:18][NH:19]C(=O)OC(C)(C)C)[CH:14]=[CH:15][CH:16]=2)[NH:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[C:13]([C:17]([CH3:29])([CH2:27][CH3:28])[CH2:18][NH2:19])[CH:14]=[CH:15][CH:16]=2)[NH:4][N:3]=1tert-butyl 2-(3-(3-chloro-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylbutylcarbamate (60 mg, 0.1446 mmol) was dissolved in dry DCM (2 mL) and cooled in an ice-bath. TFA (2 mL,) was added slowly dropwise and the resultant was stirred at 0° C. for ˜25 minutes and at RT for ˜45 minutes. The reaction mixture was concentrated under reduced pressure and partitioned between EtOAc and saturated Na2CO3. The aqueous layer was extracted with EtOAc (3×10 mL) and the combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a slightly yellow gum. The resulting mixture was purified by column chromatography (9% MeOH/1% NH4OH in DCM, ˜50 mL silica) to give a white solid (25.2 mg, 55% Yield).
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