Trifluoroacetic acid → HCID 178489375, compound

Participants

Reaction Steps

To the crude 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 TFA (2 mL) and the resulting mixture was sonicated till the residue was completely dissolved. The TFA was evaporated. The residue was treated with ethylene diamine (0.2 mL) to scavenge the formaldehyde which generated from the de-protection of the trimethylsilanylethoxymethyl group. The resulting mixture was sonicated till the residue was completely dissolved to give a greenish blue solution. DMSO was added to make a 2 mL solution which was used in preparative LCMS purification on a reverse phase column to yield 2-{3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-N,N-dimethyl-acetamide as a white solid (21 mg, 29% over two steps) MS: m/z 387 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 2.84 (s, 3H), 3.04 (s, 3H), 3.78 (s, 2H), 3.86 (s, 6H), 7.10 (t, 1H), 7.23 (d, 1H), 7.25 (d, 1H), 7.43 (t, 1H), 7.47 (t, 1H), 7.61 (s, 1H), 7.62 (d, 1H), 7.66 (d, 1H), 8.30 (s, 1H), 8.82 (d, sH), 13.82 (s, 1H).

Provenance & Evidence