Hydrogen Peroxide → HCID 135899514, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (70%, 0.66 mL, ca. 13.2 mmol) was added dropwise to a stirred solution of TFAA (1.9 mL, 13.2 mmol) in DCM (10 mL) at 0° C. The solution was stirred at 0° C. for 5 min, warmed to 20° C. for 10 min, then cooled to 0° C. and added to a stirred solution of 1-oxide 197 (363 mg, 1.3 mmol) and TFA (0.51 mL, 6.6 mmol) in DCM (15 mL) at 0° C. The solution was stirred at 20° C. for 4 h, diluted with dilute aqueous NH3 solution (10 mL) and extracted with CHCl3 (4×50 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 198 (98 mg, 25%) as a red solid: mp (MeOH/EtOAc) 149-151° C.; 1H NMR δ 8.12 (s, 1H, H-5), 7.54 (s, 1H, H-9), 7.27 (br s, 1H, NH), 4.75 (t, J=8.3 Hz, 2H, H-7), 3.58-3.64 (m, 2H, CH2N), 3.43 (t, J=8.2 Hz, 2H, H-6), 2.62 (t, J=6.0 Hz, 2H, CH2N), 2.31 [s, 6H, N(CH3)2]; 13C NMR δ 159.9, 148.9, 141.6, 135.2, 130.9, 113.1, 97.4, 72.4, 57.5, 45.1 (2), 38.8, 29.7. Anal. calcd for C13H17N5O3.¼H2O: C, 52.8; H, 6.0; N, 23.7. Found: C, 52.8; H, 5.7; N, 23.5%.

Provenance & Evidence