Diisopropylethylamine → HCID 178452336, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-chloro-2-phenylethanone (0.38 g, 0.94 mmol) in 1,4-dioxane (15 mL) was added Hunig's Base (0.50 mL, 2.82 mmol) and tert-butyl piperazine-1-carboxylate (0.349 g, 1.88 mmol). The reaction mixture was heated at 100° C. for 16 hours. The solvent was removed under reduced pressure and the crude product was purified using (SiO2, gradient from 80% EtOAc in hexanes to 100% EtOAc in hexane) to give the desired product, 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 as a white solid (0.188 g, 41%). M.p.=159-161° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.95 (s, 1H), 8.41 (s, 1H), 7.46-7.2 (m, 5H), 5.07-4.65 (m, 3H), 4.0-3.7 (m, 2H), 3.3-3.1 (m, 5H), 2.95-2.85 (m, 1H), 2.53-2.3 (m, 4H), 1.35 (s, 9H); LCMS [M+H]: 555.

Provenance & Evidence