HCID 10093591, compound → 5-[(3-Ethyl-5-(2-[3-(methylsulfonyl)phenoxy]ethyl]-1H-pyrazol-4-yl)oxy]isophthalonitrile

HRID 1352718Notes

Reaction equation

HRID 1352718 reaction equation
[CH2:1]([C:3]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([C:17]#[N:18])[CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])=[C:6]([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([CH3:30])=[O:29])[CH:23]=2)[NH:5][N:4]=1)[CH3:2].[OH:31]OS([O-])=O.[K+]>CO.O>[CH2:1]([C:3]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([C:17]#[N:18])[CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])=[C:6]([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([CH3:30])(=[O:31])=[O:29])[CH:23]=2)[NH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 10093591HCID 10093591, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 100945615-[(3-Ethyl-5-(2-[3-(methylsulfonyl)phenoxy]ethyl]-1H-pyrazol-4-yl)oxy]isophthalonitrileYield 34.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of the sulfoxide from Example 5 (34 mg, 0.08 mmol) in methanol (1 ml) was added a solution of oxone (49 mg, 0.08 mmol) in water (1 ml). After 2 hours the reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (5 ml) and water (5 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product mixture was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (100:0, 99:1 then 98:2, by volume) to give the title compound as a colourless oil (12 mg).

Workup

  1. concentrationAfter 2 hours the reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between dichloromethane (5 ml) and water (5 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product mixture was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (100:0, 99:1

Sources & evidence

ORD record
ord-3eb6d4de358c4d4abf8990cf23fbbb4d
Source dataset
uspto-grants-2007_05
Patent number
US07220772B2

Reaction notes

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