Hydrogen Peroxide → HCID 178438079, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (70%, 0.5 mL, ca. 5 mmol) was added dropwise to a stirred solution of TFM (0.7 mL, 5 mmol) in DCM (10 mL) at 0° C. The solution was stirred at 20° C. for 10 min, then cooled to 0° C., added to a solution of 1-oxide 264 (120 mg, 0.5 mmol) and TFA (0.19 mL, 2.5 mmol) in DCM (10 mL) at 0° C. The solution was stirred at 20° C. for 4 h, diluted with dilute aqueous NH3 solution (20 mL) and extracted with DCM (4×100 mL). The combined organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (2-8%) of MeOH/DCM, to give 1,4-dioxide 265 (24 mg, 19%) as a red solid: mp 117-121° C.; 1H NMR δ 8.35 (d, J=8.8 Hz, 1H, H-5), 7.70 (d, J=8.8 Hz, 1H, H-6), 4.41 (s, 2H, H-10), 3.18 (q, J=7.5 Hz, 2H, CH2), 3.12 (br t, J=5.8 Hz, 2H, H-7), 2.74 (t, J=5.8 Hz, 2H, H-8), 2.58 (s, 3H, NCH3), 1.42 (t, J=7.5 Hz, 3H, CH3); MS (APCI) m/z 261 (MH+, 100%); HRMS (FAB+) calcd for C13H17N4O2 (MH+) m/z 261.1352, found: 261.1354.

Provenance & Evidence