Dichloromethane → N-(4-methoxybiphenyl-3-yl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

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Reaction Steps

To a solution of the 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate (0.06 g, 0.15 mmol) and Hunig's Base (0.2 mL) in dichloroethane (2 mL) was added 3-isocyanato-4-methoxybiphenyl (0.034 g, 0.15 mmol). The mixture was stirred at room temperature for 24 hours before being poured into dichloromethane (50 mL) and washed with water (100 mL). The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give an off white solid. Trituration with diethylether (20 mL) gave N-(4-methoxybiphenyl-3-yl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide as an off white powder (0.030 g, 40%). M.p.=148-151° C. 1H NMR (DMSO-d6) 400 MHz δ 8.37 (s, 1H), 8.18 (s, 1H), 7.96 (s, 1H), 7.58-7.30 (m, 6H), 7.10 (d, J=8.4 Hz, 1H), 4.80 (s, 2H), 3.87-3.83 (m, 5H), 3.17 (s, 2H). LCMS [M+H]: 400.

Provenance & Evidence