Water → HCID 60133240, compound

HRID 1716614Notes

Reaction equation

HRID 1716614 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-0e1498a1e5c34530b8b6a0b7732f6f8c
Source dataset
uspto-grants-2010_09
Patent number
US07803832B2

Reaction notes

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