Phenyl isocyanate → 3-(4-methoxybenzyl)-N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

Participants

Reaction Steps

To a solution of 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (0.075 g, 0.256 mmol) in dichloromethane (3 mL) was added phenyl isocyanate (31 μL, 0.281 mmol). The reaction mixture was shaken at room temperature for 1 hour. The solvent was then removed under reduced pressure to give 3-(4-methoxybenzyl)-N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide as a tan solid (LCMS [M+H]:414), which was used for next step without further purification. White solid; M.p.=>65° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.72 (s, 1H), 8.41 (s, 1H), 8.20 (s, 1H), 7.51-7.45 (m, 2H), 7.28-7.15 (m, 4H), 6.98-6.91 (m, 1H), 6.88-6.82 (m, 2H), 5.59 (s, 2H), 4.79 (s, 2H), 3.82 (t, 6.4 hz, 2H), 3.67 (s, 3H), 3.14 (t, J=J=6.4 Hz, 2H); LCMS [M+H]: 414.6.

Provenance & Evidence