Trifluoroacetic acid → HCID 86645580, compound

Participants

Reaction Steps

Synthesis of (S)-2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethanaminium 2,2,2-trifluoroacetate. To a solution of (S)-tert-butyl 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethylcarbamate (0.23 g, 0.43 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (3 mL). The reaction was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the crude product was purified using reverse phase HPLC to give the pure desired product (S)-2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethanaminium 2,2,2-trifluoroacetate as a pale yellow solid (0.131 g, 50%). M.p.>115° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.60 (brs, 2H), 8.45/8.15 (s, 1H, rotamers), 8.12/8.08 (s, 1H, rotamers), 7.55-7.33 (m, 5H), 7.17 (m, 2H), 6.82 (m, 2H), 5.75 (m, 1H), 5.55 (s, 2H), 4.97-4.35 (m, 2H), 4.02/3.74 (m, 2H, rotamers), 3.01/2.30 (m, 2H, rotamers); LC-Mass: m/e 428.57 (M+H). LCMS [M+H]: 428.

Provenance & Evidence