HCID 59504717, compound → HCID 25121168, compound

Participants

Reaction Steps

A solution of 4-(4-tert-butylphenyl)-2-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-4,5-dihydro-1,3-oxazole (Example 70, 100 mg, 0.26 mmol) in THF (2 mL) was treated with manganese dioxide (45 mg, 0.52 mmol), and the resultant mixture was stirred to reflux. Further portions of manganese dioxide (45 mg and 90 mg) were added after 2.5 and 4.5 h. After a total of 6.5 h, the mixture was cooled to rt, diluted with 2 ml THF and filtered over a pad of celite. The filtrate was concentrated in vacuo, re-disolved in dichloromethane and successively washed with aqueous HCl (1.0 N) and water, dried (MgSO4), filtered, and concentrated to dryness. The crude material was purified by flash chromatography (silica) eluting with cyclohexane/ethyl acetate 2:1. The combined product fractions were then further purified by preparative HPLC to afford the title compound as a white solid (49 mg, 50%): 1H NMR (400 MHz, DMSO-d5) δ 8.58 (s, 1H), 7.75 (d, 2H), 7.47 (d, 2H), 7.18 (d, 2H), 7.08 (d, 2H), 6.67 (s, 1H), 5.37 (s, 2H), 2.29 (s, 3H), 2.28 (s, 3H), 1.31 (s, 9H); ES-MS m/z 386, HPLC RT (Method E) 2.81 min.

Provenance & Evidence