Hydrogen Peroxide → HCID 135899478, compound

Temperature

0 °C

H2O2 (70%, 0.67 mL, ca. 13.5 mmol) was added dropwise to a stirred solution of TFAA (1.9 mL, 13.5 mmol) in DCM (20 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 223 (374 mg, 1.4 mmol) and TFA (0.52 mL, 6.7 mmol) in DCM (15 mL) at 0° C. The solution was stirred at 20° C. for 8 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 (0-20%) of MeOH/DCM, to give 1,4-dioxide 224 (52 mg, 13%) as a red solid: mp (MeOH/EtOAc) 175-179° C.; 1H NMR δ 7.60 (s, 1H, H-9), 7.59 (s, 1H, H-5), 7.35 (br s, 1H, NH), 6.21 (s, 2H, H-7), 3.61 (br t, J=6.0 Hz, 2H, CH2N), 2.62 (br t, J=6.0 Hz, 2H, CH2N), 2.31 [s, 6H, N(CH3)2]; 13C NMR δ 155.9, 149.7, 148.9, 137.8, 126.7, 103.5, 97.9, 94.1, 57.4, 45.1 (2), 38.8. Anal. calcd for C12H15N5O4.½CH3OH: C, 48.5; H, 5.5; N, 22.6. Found: C, 48.7; H, 5.3; N, 22.6%.

1. temperaturewarmed to 20° C. for 10 min
2. temperaturecooled to 0° C.
3. stirringThe solution was stirred at 20° C. for 8 h
4. extractionextracted with CHCl3 (4×50 mL)
5. customThe combined organic fraction was dried
6. customthe solvent evaporated
7. customThe residue was purified by chromatography
8. washeluting with a gradient (0-20%) of MeOH/DCM

ORD record

ord-379c9d4e576240a7a9895df6e206c0a2

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989451B2