2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 73330644, compound

Participants

Reaction Steps

To a suspension of 2-(4-methyl-5-(3-(4-methylpiperazin-1-yl)benzyl)thiazol-2-yl)-4-phenyl-4,5-dihydrooxazole (17 mg, 0.04 mmol) and MnO2 (21 mg, 0.24 mmol) in toluene (2 mL), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (5 mg, 0.02 mmol) was added. The mixture was refluxed for 48 h under N2, and then cooled. The precipitate was filtered and washed with DCM/MeOH (10/1, 30 mL). The filtrate was washed with NaHCO3 (2 M, 10 mL) and brine (10 mL), dried over Na2SO4, filtered, concentrated and purified by prep-TLC (DCM:MeOH=15:1) to afford 2-(4-methyl-5-(3-(4-methylpiperazin-1-yl)benzyl)thiazol-2-yl)-4-phenyloxazole as a light yellow solid (1.0 mg, 5%). MS (ES+) C25H26N4OS requires: 430, found: 431[M+H]+. 1H-NMR (500 MHz, CDCl3) δ ppm 7.98 (s, 1H), 7.80 (d, J=9.5 Hz, 2H), 7.41 (t, J=7.5 Hz, 2H), 7.34 (t, J=7.5 Hz, 1H), 7.22 (t, J=7.5 Hz, 1H), 6.80-6.82 (m, 1H), 6.72-6.78 (m, 2H), 4.10 (s, 2H), 3.28 (br, 4H), 2.72 (br, 4H), 2.50 (s, 3H), 2.45 (s, 3H).

Provenance & Evidence