Water → HCID 9846451, compound

HRID 992268Notes

Reaction equation

HRID 992268 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([C:9]1[C:10]([CH3:31])=[C:11]([S:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[C:12](=[O:22])[N:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:14]=1)(=[O:8])[CH3:7].O>N1C=CC=CC=1>[C:6]([C:9]1[C:10]([CH3:31])=[C:11]([S:23][C:24]2[CH:25]=[CH:26][C:27]([NH:30][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:28][CH:29]=2)[C:12](=[O:22])[N:13]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[N:14]=1)(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 18412001HCID 18412001, compound

Product 1

HCID 9846451HCID 9846451, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (0.1 ml) was added to a solution of 6-acetyl-4-(4-aminophenylthio)-2-(4-fluorophenyl)-5-methyl-3(2H)-pyridazinone (185 mg) in pyridine (2 ml) at 5° C., followed by stirring at room temperature for 1 hour. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. After washing with a saturated aqueous sodium hydrogen carbonate solution and a brine, the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1), and was crystallized from ether to obtain 6-acetyl-2-(4-fluorophenyl)-5-methyl-4-(4-methylsulfonylaminophenylthio)-3(2H)-pyridazinone (180 mg) (Compound No. 4-01).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washAfter washing with a saturated aqueous sodium hydrogen carbonate solution
  3. dry with materiala brine, the organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by evaporation
  5. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)
  6. customwas crystallized from ether

Sources & evidence

ORD record
ord-29c4a8a12265425f8ce2ace5fd3d8999
Source dataset
uspto-grants-2002_10
Patent number
US06469003B1

Reaction notes

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