Sodium Thiosulfate → HCID 57940688, compound

HRID 1437291Notes

Reaction equation

HRID 1437291 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]([C:27]2[CH:31]=[C:30]([C:32]3[CH:37]=[C:36](SC)[CH:35]=[CH:34][N:33]=3)[N:29]([C:40]3[CH:41]=[N:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=3)[N:28]=2)=[O:26])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[S:48]([O-:52])([O-])(=[O:50])=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]([C:27]2[CH:31]=[C:30]([C:32]3[CH:37]=[C:36]([S:48]([CH3:2])(=[O:52])=[O:50])[CH:35]=[CH:34][N:33]=3)[N:29]([C:40]3[CH:41]=[N:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=3)[N:28]=2)=[O:26])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 57940615HCID 57940615, compound

Product 1

HCID 57940688HCID 57940688, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 3-chloroperbenzoic acid (0.260 g) was added to a solution of 4-[1-(6-methoxy-3-pyridyl)-5-(4-methylthio-2-pyridyl)pyrazole-3-carbonyl]piperazine-1-carboxylic acid tert-butyl ester (0.366 g) obtained in Example 47 in methylene chloride (7.3 mL), and the mixture was stirred for 20 minutes. Subsequently, the mixture was stirred at room temperature for a further 2 hours. At 0° C., 3-chloroperbenzoic acid (0.124 g) was added thereto, and the resultant mixture was stirred for 2 hours. Saturated aqueous sodium thiosulfate (10 mL) and saturated aqueous sodium hydrogencarbonate (10 mL) were added to the reaction mixture, followed by stirring. The reaction mixture was partitioned between water and chloroform. The organic layer was dried over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as an amorphous product (0.387 g, 99%).

Workup

  1. stirringSubsequently, the mixture was stirred at room temperature for a further 2 hours
  2. stirringby stirring
  3. customThe reaction mixture was partitioned between water and chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-03db52cf3c6f430dba8e7930b29be409
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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