HCID 59490674, compound → HCID 46836975, compound

Participants

Reaction Steps

A solution of 3-(4-methoxybenzyl)-3,6,7,8-tetrahydrobenzo[6,7]cyclohepta[1,2-d]pyrazolo[3,4-b]pyridine (2.0 g, 5.63 mmol) in trifluoroacetic acid (10 mL) was heated at 100° C. for 6 hours. On completion of the reaction, the solvent removed under reduced pressure. The residue was dissolved in water (20 mL) and then it was basified to pH=10 using ammonium hydroxide. The aqueous layer was extracted with 10% methanol in dichloromethane (2×100 mL). The organic extracts were combined, dried using sodium sulfate and concentrated under reduced pressure. The crude product was purified using flash column chromatography (SiO2, gradient 100% dichloromethane to 2% methanol in dichloromethane) to give the pure desired product (0.9 g, 68%) as off-colored solid. 1H NMR (DMSO-d6, 400 MHz): δ 13.58 (s, 1H), 8.14 (s, 1H), 8.10 (s, 1H), 7.66 (t, J=8.0 Hz, 1H), 7.44-7.36 (m, 3H), 7.32 (t, J=8.0 Hz, 1H), 2.60-2.38 (m, 4H), 2.15 (quintet, 3H); LCMS [M+H]: 236.

Provenance & Evidence