Hydrochloric Acid → HCID 178520218, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-(2-(1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethyl)piperazine-1-carboxylate (0.075 g, 0.17 mmol) in dichloromethane (12 mL) and 1,4-dioxane (6 mL) was added a 4 M solution of HCl gas in 1,4-dioxane (0.82 mL, 3.4 mmol). The reaction was shaken at room temperature for 16 hours. During the reaction a pale tan solid precipitate was formed. The solvent was removed under reduced pressure to give the pure desired product, 4-(2-(1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethyl)piperazin-1-ium chloride (0.064 g, 71%) as an tan solid. M.p.>245° C.; 1H NMR (400 MHz, DMSO-d6) δ13.98 (s, 1H), 9.92 (brs, 2H), 8.44/8.21 (s, 1H, rotamers), 7.44-7.68 (m, 5H), 6.28 (m, 1H), 4.75-4.92 (m, 2H), 4.11 (m, 8H), 3.90 (m, 1H), 3.66 (m, 1H), 3.29 (m, 1H), 2.62 (m, 1H); LCMS [M+H]: 455.

Provenance & Evidence