HCID 25121515, compound → HCID 25121516, compound

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A solution of 4-(4-cyclohex-1-en-1-ylphenyl)-2-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,3-oxazole (Example 80, 30 mg, 0.073 mmol) in ethanol (1.5 ml) was hydrogenated in a continuous-flow reactor (H-cube, Thales Nano, Hungary) at an hydrogen pressure of 1 bar at rt with a flow rate of 1 ml/min using palladium (10% on charcoal) as a stationary phase. After evaporation of the solvent, the crude material was purified by preparative HPLC to afford the title compound as a white solid (13 mg, 43%): 1H NMR (400 MHz, DMSO-d6) 8.57 (s, 1H), 7.72 (d, 2H), 7.29 (d, 2H), 7.17 (d, 2H), 7.07 (d, 2H), 6.67 (s, 1H), 5.36 (s, 2H), 3.51-3.40 (m, 1H), 2.29 (s, 3H), 2.28 (s, 3H), 1.82-1.69 (m, 4H), 1.48-1.22 (m, 6H); ES-MS m/z 412, HPLC RT (Method D) 3.52 min.

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