Hydrogen Peroxide → HCID 178438081, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (70%, 0.95 mL, ca 16 mmol) was added drop-wise (over 10 min) to a stirred solution of 1-oxide 143 (503 mg, 1.6 mmol), TFAA (2.56 mL, 16.0 mmol) and TFA (0.66 mL, 8.0 mmol) in DCM (60 mL) at 20° C. and the mixture was stirred at 20° C. for 7 h. Dilute Na2CO3 solution (40 mL) was added and the mixture was extracted with DCM (5×80 mL). The combined organic fraction was dried and the solvent evaporated to give an oil which was purified by chromatography, eluting with a gradient (0-2%) of MeOH/DCM, to give 1,4-dioxide 144 (87 mg, 21%) as a yellow solid: mp (MeOH/DCM) 164-165° C.; 1H NMR δ 8.31 (s, 1H, H-9), 8.25 (s, 1H, H-5), 3.72 (t, J=4.6 Hz, 4H, 2×CH2O), 3.17-3.34 (m, 4H, CH2), 2.80-2.95 (m, 3H, CH2, H-7), 2.45 (t, J=4.6 Hz, 4H, 2×CH2N), 2.38 (d, J=7.7 Hz, 2H, CH2), 1.43 (t, J=7.5 Hz, 3H, CH3); 13C NMR δ 155.7, 154.1, 149.5, 139.2, 134.0, 116.3, 114.3, 67.0 (2), 63.1, 53.9 (2), 37.7, 37.2, 36.6, 23.8, 9.2. Anal. calcd for C17H22N4O3: C, 61.8; H, 6.7; N, 17.0. Found: C, 62.1; H, 6.7; N, 16.8%.

Provenance & Evidence