Toluene → 1-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone

Participants

Reaction Conditions

Reaction Steps

To 1-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone (0.203 g, 0.49 mmol) was added trifluoroacetic acid (2 mL). The reaction was heated at 70° C. for 18 hours. To the crude reaction mixture was added toluene (5 mL) and the resulting mixture was evaporated under reduced pressure to give a crude product. The residue was diluted in dichloromethane (4 mL/mmol) and washed with saturated aqueous sodium carbonate. The combined aqueous layers were washed with dichloromethane. The combined organics extract was dried over Na2SO4 and concentrated under reduced pressure to give a brown oil. The oily residue was triturated with a mixture of dichloromethane and methanol to yield the desired product, 1-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone as an off-white solid (0.041 g, 18%). M.p.=164-166° C.; 1H NMR (DMSO-d6), 400 MHz) δ 13.57 (s, 1H), 8.36 (s, 1H), 8.12 (s, 1H), 7.27 (m, 5H), 4.87 (s, 1H), 4.77 (s, 1H), 3.82-3.86 (m, 4H), 3.01 (m, 2H); LCMS [M+H]: 293.

Provenance & Evidence