m-Chloroperbenzoic acid → HCID 69331470, compound

HRID 915045Notes

Reaction equation

HRID 915045 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[NH2:12][C:13]1[N:14]=[C:15]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:16]([C:22]2[CH:23]=[CH:24][C:25](=[O:31])[N:26]([CH:28]([CH3:30])[CH3:29])[N:27]=2)=[N:17][C:18]=1[S:19]([CH3:21])=[O:20]>C(Cl)Cl>[NH2:12][C:13]1[N:14]=[C:15]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:16]([C:22]2[CH:23]=[CH:24][C:25](=[O:31])[N:26]([CH:28]([CH3:30])[CH3:29])[N:27]=2)=[N:17][C:18]=1[S:19]([CH3:21])(=[O:9])=[O:20]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69332706HCID 69332706, compound

Product 1

HCID 69331470HCID 69331470, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

Under ice-cooling, m-chloroperbenzoic acid (70-75% purity) (530 mg) was added to a mixture of 6-[5-amino-6-(methylsulfinyl)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (750 mg) in CH2Cl2 (7.5 ml). The mixture was stirred at 25-30° C. for 5 hours, washed with saturated aq. sodium thiosulfate, saturated aq. NaHCO3 and brine, dried over MgSO4 and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (30:70 v/v) to give 6-[5-amino-6-(methylsulfonyl)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone as a solid (524 mg).

Workup

  1. temperatureUnder ice-cooling
  2. washwashed with saturated aq. sodium thiosulfate, saturated aq. NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue
  6. customThe residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (30:70 v/v)

Sources & evidence

ORD record
ord-2a8903a75c4e439695edfe4af61ca74d
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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