Pyrazole → HCID 53236426, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[(5-bromopyridin-2-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]-4-oxo-4H-quinolizine-3-carboxamide (Example 2, 0.045 g, 0.099 mmol) and pyrazole (0.020 g, 0.30 mmol) in 2 mL of DMSO under an atmosphere of nitrogen was added aqueous cesium carbonate (1 M, 0.20 mL, 0.20 mmol), trans-N, N-dimethylcyclohexane-1,2-diamine (0.014 g, 0.10 mmol), and copper(I) iodide (0.014 g, 0.076 mmol). The mixture was heated at 120° C. for 15 h, cooled to rt, and subjected to purification via reverse phase HPLC to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 444.0 for [M+H]+: 1H NMR (400 MHz, CD3OD) δ 9.46 (d, J=7.6 Hz, 1H), 8.93 (s, 1H), 8.58 (s, 1H), 8.28 (s, 1H), 8.17-8.08 (m, 2H), 7.85-7.82 (m, 1H), 7.75 (s, 1H), 7.49-7.44 (m, 2H), 6.56-6.55 (m, 1H), 4.53 (s, 2H), 3.86-3.82 (m, 1H), 3.74-3.70 (m, 1H), 2.13-2.02 (m, 2H), 1.89-1.73 (m, 13H), 1.43-1.33 (m, 3H).

Provenance & Evidence