Trifluoroacetic acid → HCID 59490623, compound

Participants

Reaction Conditions

Reaction Steps

To 3,7-bis-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (0.092 g, 0.22 mmol) was added trifluoroacetic acid (3 mL). The reaction mixture was heated at 65° C. for 16 hours. On the completion of the reaction, toluene (5 mL) was added. The solvent was removed under reduced pressure to give a dark brown solid. The residue was then partitioned between EtOAc and aqueous NaOH. The organic layer was then separated, washed with brine (2×10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give a residue. The crude product was purified using flash column chromatography (SiO2, 1% methanol in EtOAc) to desired product, 7-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine as a pale yellow solid (0.047 g, 72%). M.p.=184-186° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.49 (s, 1H), 8.19 (s, 1H), 8.08 (s, 1H), 7.32-7.26 (m, 2H), 6.94-6.88 (m, 2H), 3.75 (s, 3H), 3.64 (s, 2H), 3.62 (s, 2H), 3.1-3.03 (m, 2H), 2.8-2.72 (m, 2H); LCMS [M+H]: 295.

Provenance & Evidence