Hydrochloric Acid → 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylacetic acid

Participants

Reaction Steps

To a solution of ethyl 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylacetate (0.116 g, 0.25 mmol) in methanol (3 mL) was added 1.5 M NaOH (1.67 mL, 2.5 mmol). The reaction mixture was stirred at room temperature for 16 hours. The reaction was then acidified to pH 2-3 using 1N HCl. The mixture was then extracted with dichloromethane (3×20 mL). The organic extracts were combined, dried (Na2SO4), filtered and concentrated under reduced pressure to afford the pure desired product 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylacetic acid as an off-white solid; (0.095 g, 87%). M.p. 130-145° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.34 (s, 1H), 8.17 (s, 1H), 7.53 (m, 5H), 7.18 (m, 2H), 6.84 (m, 2H), 5.57 (s, 2H), 4.85 (m, 1H), 4.05 (m, 2H), 3.68 (s, 3H), 3.21 (m, 4H); LCMS [M+H]: 429.

Provenance & Evidence