Trifluoroacetic acid → HCID 178489383, compound
Reaction equation
[OH:1][CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[N:21][N:20](COCC[Si](C)(C)C)[C:17]3=[N:18][CH:19]=2)[CH:9]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4].FC(F)(F)C(O)=O>>[OH:1][CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[N:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH:9]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4]Participants
3
Procedure
To the crude 2-hydroxy-2-{3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanylethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-N,N-dimethyl-acetamide obtained in last step was added trifluoroacetic acid (2 mL) and the resulting mixture was sonicated until the residue was completely dissolved. The trifluoroacetic acid was evaporated and the residue treated with ethylene diamine (0.2 mL). The resulting mixture was purified via mass-triggered reverse-phase HPLC to yield 2-hydroxy-2-{3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-N,N-dimethyl-acetamide as a white solid (25 mg, 33% over two steps). MS: m/z 403 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 2.89 (d, 6H), 3.87 (s, 3H), 5.48 (d, 1H), 5.57 (d, 1H), 7.10 (t, 1H), 7.24 (d, 1H), 7.38 (d, 1H), 7.47 (dt, 1H), 7.48 (t, 1H), 7.67 (dd, 1H), 7.70 (d, 1H), 7.75 (s, 1H), 8.32 (d, 1H), 8.84 (d, 1H), 13.84 (s, 1H).