Perchloric Acid → HCID 178489411, compound

Participants

Reaction Steps

2-Hydroxy-2-{5-[3-(2-methoxyphenyl)-1-(2-trimethylsilanylethoxymethyl)-1H-pyrazolo[3,4-b]pyridin5-yl]-pyridin-3-yl}-N,N-dimethylacetamide (374 mg, 0.702 mmol) was treated with 5% v/v of 70% perchloric acid in glacial acetic acid (5 mL) for 2 h. The solids were collected by filtration and were dissolved in ethyl acetate upon shaking with saturated sodium bicarbonate. The layers were separated and the organics were dried over sodium sulfate and concentrated in vacuo. The material was dissolved in dichloromethane (1 mL) and treated with N,N-dimethylethylenediamine (154 μL) for 2.5 h. The mixture was concentrated and the residue was dissolved in dimethylsulfoxide and purified by preparative HPLC to afford 2-hydroxy-2-{5-[3-(2-methoxyphenyl)-1H-pyrazolo[3,4-b]pyridin5-yl]-pyridin-3-yl}-N,N-dimethylacetamide (10 mg, 0.025 mmol). 1H-NMR (500 MHz, dimethylsulfoxide-d6) δ 2.79 (s, 3H), 2.92 (s, 3H), 3.79 (s, 3H), 5.52 (m, 1H), 5.78 (m, 1H), 7.03 (t, J=7.0 Hz, 1H), 7.17 (d, J=8 Hz, 1H), 7.40 (dt, J=1, J=6.5 Hz, 1H), 7.59 (dd, J=1.5, J=7.5 Hz, 1H), 8.04 (t, J=2.5 Hz, 1H), 8.33 (d, J=2.5 Hz, 1H), 8.52 (d, J=2.0 Hz, 1H), 8.81 (d, J=2.0 Hz, 1H), 8.85 (d, J=2.5 Hz, 1H). MS: m/z 404 (M+H+).

Provenance & Evidence