Hydrogen Peroxide → HCID 135899491, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (70%, 0.50 mL, ca. 10 mmol) was added dropwise to a stirred mixture of 1-oxide 249 (328 mg, 1.4 mmol), TFA (4 mL) and water (0.3 mL) at 0° C. and the mixture was stirred at 20° C. Two more aliquots of H2O2 (70%, 0.50 mL, ca. 10 mmol) were added at 3 h and 20 h. After 28 h at 20° C., the mixture was diluted with aqueous NH3 solution (20 mL) and extracted with DCM (5×50 mL). The combined organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1,4-dioxide 250 (68 mg, 19%) as a red solid which was crystallised as the hydrochloride salt: mp (MeOH/DCM) 230° C.; 1H NMR [(CD3)2SO] δ 11.84 (br s, 1H, HCl), 8.27 (s, 1H, H-9), 8.20 (s, 1H, H-5), 8.14 (br s, 2H, NH2), 4.88-5.05 (m, 2H, CH2N), 4.50-4.73 (m, 2H, CH2N), 3.42 (q, J=7.2 Hz, 2H, CH2N), 1.32 (t, J=7.2 Hz, 3H, CH3); 13C NMR [(CD3)2SO] δ 151.4, 143.0, 138.5, 134.0, 130.6, 115.6, 111.4, 56.5, 56.1, 49.1, 10.3; HRMS (FAB+) calcd for C11H14N5O2 (MH+) m/z 248.1148, found 248.1154.

Provenance & Evidence