Dichloromethane → n-(3-Benzylphenyl)-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 (0.08 g, 0.2 mmol) in 1,2-dichloroethane (2 mL) was added Hunig's Base (0.2 mL) followed by 1-benzyl-3-isocyanatobenzene (40 μl, 0.2 mmol). The mixture was stirred at room temperature for 2 hours before being diluted with water (50 mL) and extracted with dichloromethane (2×50 mL). The organic extracts were dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give a pale yellow oil. A minimum amount of dichloromethane was added and N-(3-benzylphenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide crystallized out as a white solid (0.038 g, 36%). M.p.=175-178° C. 1H NMR (DMSO-d6) 400 MHz δ 8.66 (s, 1H), 8.33 (s, 1H), 8.16 (s, 1H), 7.33-7.13 (m, 8H), 6.83 (d, J=7.6 Hz, 1H), 4.75 (s, 2H), 3.88 (s, 2H), 3.80 (d, J=5.2 Hz, 2H). LCMS [M+H]: 384.

Provenance & Evidence