Pyrazole → HCID 86682405, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-5-[(6-chloropyridin-3-yl)methyl]-2-[trans-2-hydroxycyclohexyl]-1,2-dihydro-3H-pyrrolo[3,4-c]isoquinoline-3-one (Example 16, 0.040 g, 0.098 mmol) and pyrazole (0.020 g, 0.29 mmol) in 1 mL of dimethylsulfoxide under an atmosphere of nitrogen was added cesium carbonate (1.0 M aqeuous, 0.20 mL, 0.20 mmol), (±)-trans-N,N′-dimethylcyclohexane-1,2-diamine (1.4 mg, 0.0098 mmol), and copper(I) iodide (0.93 mg, 0.0049 mmol). The mixture was heated at 120° C. for 15 hr, cooled to ambient temperature, and purified via preparative reverse phase HPLC to provide the titled compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 440.9 for [M+H]+: 1H NMR (400 MHz, CD3OD) δ 8.51-8.46 (m, 3H), 8.14 (d, J=8.2 Hz, 1H), 7.94-7.80 (m, 5H), 6.54-6.44 (m, 1H), 4.90 (s, 2H), 4.12-4.08 (m, 1H), 3.93-3.86 (m, 1H), 3.49-3.40 (m, 1H), 3.31 (s, 2H), 2.20-2.02 (m, 1H), 1.95-1.90 (m, 1H), 1.89-1.70 (m, 3H), 1.54-1.43 (m, 3H) ppm.

Provenance & Evidence