Trifluoroacetic acid → 3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine

Participants

Reaction Steps

To a solution of tert-butyl 3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate (3.5 g, 8.8 mmol) in dichloromethane (35 mL) at room temperature was added trifluoroacetic acid (5.04 g, 44.4 mmol) in a drop wise manner. The reaction mixture was stirred at room temperature for 5 hours. Once the reaction was complete the solvent was removed under reduced pressure and the resulting residue was triturated with diethyl ether to give a solid. The solid was filtered, washed with diethyl ether and dried under reduce pressure. The dried solid was then dissolved in water and basified with saturated Na2CO3 solution. The aqueous layer was extracted with 10% methanol in CH2Cl2 (3×150 mL). The organic extracts were combined, dried using sodium sulfate, filtered and concentrated under reduced pressure to give a residue. The residue was triturated with hexane to afford the pure desired product 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine as a white solid (2.1 g, 80%). M.p.=96-102° C. 1H NMR (400 MHz, CDCl3) δ 8.22 (s, 1H), 7.93 (s, 1H), 7.26 (d, J=8.4 Hz, 2H), 6.80 (d, J=8.4 Hz, 2H), 5.61 (s, 2H), 4.11 (s, 2H), 3.73 (s, 3H), 3.219 (t, J=6 Hz, 2H), 3.016 (t, J=6 Hz, 2H) LCMS [M+H]: 295.

Provenance & Evidence