Potassium Carbonate → HCID 86660000, compound

Participants

Reaction Steps

Ethyl 8-chloro-1-[(6′-methyl-2,3′-bipyridin-5-yl)methyl]-4-thioxo-1,4-dihydrocinnoline-3-carboxylate (26 mg, 0.0058 mmol), (±)-2-hydrazinylcyclohexanol (19 mg, 0.14 mmol, 2.5 equiv) and potassium carbonate (24 mg, 0.17 mmol, 3 equiv) were combined in dimethoxyethane (1 mL) and placed into an oil bath preheated to 90° C. for 90 minutes. The mixture was cooled to ambient temperature, diluted with ethyl acetate and washed once with water and brine. The organic layer was dried sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 90:10; chloroform:methanol), providing the titled compound as a deep red solid: 1H-NMR (400 MHz, CDCl3) δ 9.02 (1H, br s), 8.56 (1H, s), 8.21 (1H, d, J=9.1 Hz), 8.16 (1H, d, J=10.9 Hz), 7.65 (2H, d, J=7.5 Hz), 7.56 (1H, d, J=9.2 Hz), 7.43 (2H, t, J=7.5 Hz), 7.27-7.21 (1H, m), 6.33 (2H, s), 4.34-4.25 (1H, m), 4.11-4.02 (1H, m), 2.6 (3H, s), 2.26-2.17 (1H, m), 2.07-2.00 (1H, m), 1.92-1.79 (2H, m), 1.68-1.56 (2H, m), 1.52-1.39 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 501.1812 [(M+H)+; calculated for C27H25ClN6O2: 501.1800].

Provenance & Evidence