Hydrogen Peroxide → HCID 135526561, compound

HRID 1669106Notes

Reaction equation

HRID 1669106 reaction equation
[OH:1]O.[CH2:3]([NH:5][C:6]1[N:7]=[N+:8]([O-:21])[C:9]2[CH:18]=[C:17]3[C:13]([CH2:14][CH:15]([CH2:19][OH:20])[CH2:16]3)=[CH:12][C:10]=2[N:11]=1)[CH3:4]>CC(O)=O.C([O-])(O)=O.[Na+]>[CH2:3]([NH:5][C:6]1[N:7]=[N+:8]([O-:21])[C:9]2[CH:18]=[C:17]3[C:13]([CH2:14][CH:15]([CH2:19][OH:20])[CH2:16]3)=[CH:12][C:10]=2[N+:11]=1[O-:1])[CH3:4]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 11952366HCID 11952366, compound

Product 1

HCID 135526561HCID 135526561, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

H2O2 (70%, 1.0 mL, ca. 20.0 mmol) was added dropwise to a stirred solution of 1-oxide 126 (71 mg, 0.27 mmol) in HOAc (3 mL) at 50° C. and the reaction was stirred at 50° C. for 20 h. The mixture was diluted with aqueous NaHCO3 solution 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 (0-4%) of MeOH/DCM, to give 1,4-dioxide 127 (11 mg, 15%) as a red solid: mp (MeOH/DCM) 153-155° C.; 1H NMR δ 8.10 (s, 1H, H-9), 8.05 (s, 1H, H-5), 7.01 (br s, 1H, NH), 3.69 (d, J=6.5 Hz, 2H, CH2O), 3.59-3.67 (m, 2H, CH2N), 3.15-3.28 (m, 2H, CH2), 2.90-3.03 (m, 2H, CH2), 2.72-2.86 (m, 1H, CH), 1.35 (t, J=7.2 Hz, 3H, CH3), OH not observed; HRMS calcd for C13H16N4O3 (M+) m/z 276.1222, found 276.1222.

Workup

  1. extractionextracted with DCM (5×50 mL)
  2. customThe combined organic fraction was dried
  3. customthe solvent evaporated
  4. customThe residue was purified by chromatography
  5. washeluting with a gradient (0-4%) of MeOH/DCM

Sources & evidence

ORD record
ord-e77f4b8d4dc14f46a570cfa0f0b53e10
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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