Benzoic Acid → HCID 67425493, compound

Participants

Reaction Steps

To 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine trifluoroaceate salt was added benzoic acid (0.064 g, 0.52 mmol), dimethyl acetamide (4 mL), dimethylformamide (2 mL) and Et3N (1.0 mL). The mixture was vortexed to ensure that the solid was fully in solution before adding HBTU (0.20 g, 0.52 mmol). The reaction mixture was shaken at room temperature for 16 hours. On completion of the reaction, EtOAc (20 mL) and 1.5M NaOH (10 mL) was added to the reaction mixture. The organic layer was separated, washed with water (2×20 mL) and concentrated under reduce pressure. The crude product was purified using flash column chromatography (SiO2, 80% EtOAc in hexanes) to give the desired product, (8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)(phenyl)methanone (0.20 g, 15%) as a white solid. M.p.=198-200° C.; 1H NMR (400 MHz, DMSO-d6) δ13.60 (s, 1H), 8.44 & 8.15 (m, 2H), 7.49 (m, 5H), 4.90 & 4.71 (m, 2H), 4.02 & 3.66 (m, 2H), 3.16 (m, 2H); LCMS [M+H]: 279.

Provenance & Evidence