Water → HCID 60133240, compound

HRID 2246692Notes

Reaction equation

HRID 2246692 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[N:21]([CH2:26]SC)[S:22]([CH3:25])(=O)=[O:23].[C:29](=O)([O-])[O-].[Na+].[Na+].O[O:36][S:37]([O-:39])=O.[K+].[OH2:41]>CC(C)=O>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:16])([F:17])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[N:21]([CH2:26][S:37]([CH3:29])(=[O:39])=[O:36])[S:22]([CH3:25])(=[O:23])=[O:41]

Participants

6

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 68517532HCID 68517532, compound

Product 1

HCID 60133240HCID 60133240, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-{5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}-N-[(methylthio)methyl]methanesulfonamide (108 mg, 0.23 mmol) in acetone (35 ml) was added sodium carbonate (318 mg, 3.04 mmol), followed by Oxone® (924 mg, 1.52 mmol) in water (12 ml). The reaction mixture was then stirred at room temperature for 5 h. To the reaction mixture was added water and the solution was extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was dissolved in a mixture of acetonitrile (1 ml) and water (1 ml) and purified by automated preparative liquid chromatography (Gilson system, 150 mm×30 mm Phenomenex LUNA C18(2) 10 μm column) using an acetonitrile:water gradient [45:55 to 95:5]. The appropriate fractions were concentrated in vacuo to give the titled compound (55 mg).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude product was dissolved in a mixture of acetonitrile (1 ml) and water (1 ml)
  6. custompurified
  7. concentrationThe appropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-94d179162f9241f692fed0aafc8dbd3d
Source dataset
uspto-grants-2010_03
Patent number
US07687533B2

Reaction notes

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