Reaktion #2470663

Reaktionsgleichung

toluene

tert-butyl 1-(3-acetamidophenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate

trifluoroacetic acid

→

1-(3-acetamidophenyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate

Ausbeute 37.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent removed under reduced pressure
2. 2
   SonstigeThe crude product was purified

Vorschrift

To a solution of tert-butyl 1-(3-acetamidophenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate (0.108 g, 0.26 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (0.5 mL). The reaction was shaken overnight at room temperature. On completion, toluene (1 mL) was added and the solvent removed under reduced pressure. The crude product was purified using reverse phase HPLC (C-18 using TFA as a modifier) to give the desired product, 1-(3-acetamidophenyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate (0.042 g, 37%) as an off-white solid; M.p.=245° C. decomposition; 400 MHz 1H NMR (DMSO-d6) δ: 13.89 (br s, 1H), 10.13 (s, 1H), 9.16 (s, 1H), 8.43 (s, 1H), 8.01 (s, 1H), 7.56-7.5 (m, 1H), 7.48-7.4 (m, 1H), 7.28-7.22 (m, 1H), 4.43 (s, 2H), 3.4-3.3 (m, 2H), 3.1-3.0 (m, 2H), 2.08 (s, 3H); LCMS [M+H]: 308.

Quelle