Hydrogen Peroxide → HCID 58072358, compound

HRID 1805696Notes

Reaction equation

HRID 1805696 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:15]=[CH:14][C:13](=[O:16])[C:12]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:20]=[CH:19][CH:18]=2)=[N:11]1)=[O:3].[OH:28]O>C(O)(=O)C>[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:15]=[CH:14][C:13](=[O:16])[C:12]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:20]=[CH:19][CH:18]=2)=[N:11]1)(=[O:28])=[O:3]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 58072497HCID 58072497, compound

Product 1

HCID 58072358HCID 58072358, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-[2-(methylsulfinyl)phenyl]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (60% purity, 300 mg, 0.80 mmol) in 20 mL of acetic acid was added 30% H2O2 aqueous solution (362 mg, 3.19 mmol), and the mixture was stirred at 40° C. for 18 h. The solvents were removed under reduced pressure, water was added, extracted with AcOEt, washed with water, Na2CO3 aqueous solution and brine, dried over Na2SO4, and then concentrated. The residue was purified by prep.-HPLC to give the title compound (20 mg, 6% yield) as a red solid: 1H NMR (400 MHz, CDCl3): δ 2.89 (3H, s), 6.60 (1H, d, J=8.0 Hz), 6.96 (1H, d, J=2.0 Hz), 7.24-7.35 (4H, m), 7.41-7.43 (2H, m), 7.70-7.77 (3H, m), 7.92 (1H, d, J=8.0 Hz), 8.16-8.18 (1H, m); LCMS (mobile phase: from 90% water and 10% CH3CN to 5% water and 95% CH3CN in 6 min, finally under these conditions for 0.5 min.) purity is >90%, Rt=3.073 min; MS Calcd.: 392. MS Found: 393 [M+H]+.

Workup

  1. customThe solvents were removed under reduced pressure, water
  2. additionwas added
  3. extractionextracted with AcOEt
  4. washwashed with water, Na2CO3 aqueous solution and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by prep.-HPLC

Sources & evidence

ORD record
ord-cc5ccdda956546f1864ea6afc991dba6
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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