Toluene → HCID 178474140, compound

Participants

Reaction Steps

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.

Provenance & Evidence