Diisopropylethylamine → HCID 59490687, compound

Participants

Reaction Steps

To a solution of 3-(6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoic acid (0.080 g, 0.24 mmol) and 1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one (0.057 g, 0.264 mmol) in dimethylacetamide (5 mL) and Hunig's Base (0.124 mL, 0.71 mmol) was added HBTU (0.107 g, 0.284 mmol). The reaction mixture was vortexed and then shaken at room temperature for 2 hours. On completion of the reaction, 1M NaHCO3 (20 mL) and EtOAc (30 mL) were added to the reaction mixture. The organic layer was separated, washed with brine (2×20 mL) and concentrated under reduced pressure to give a white solid. The white solid was washed with EtOAc and dried under reduced pressure to give the desired product, N-(3-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carbonyl)phenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide (0.035 g, 27%) as a white solid. Alternatively, the crude product can be purified either by flash column chromatography (SiO2) or reverse phase HPLC (using TFA as a modifier). White solid; M.p.=>215° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.59 (s, 1H), 10.88 (s, 1H), 8.9 (s, 1H), 8.35 (s, 1H), 8.17 (s, 1H), 7.64-7.56 (m, 2H), 7.38-7.26 (m, 2H), 7.08-6.94 (m, 4H), 4.79 (s, 2H), 4.65 (br s, 1H), 4.52-4.4 (m, 1H), 3.84 (t, J=6 Hz, 2H), 3.85-3.7 (m, 1H), 3.4-3.3 (m, 1H), 3.2-3.1 (m, 2H), 3.0-2.85 (m, 1H), 2.4-2.2 (m, 2H), 1.9-1.6 (m, 2H); LCMS [M+H]: 537.

Provenance & Evidence