3-Chloro-2-methylbenzenesulfonyl chloride → HCID 68834598, compound

HRID 490563Notes

Reaction equation

HRID 490563 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][C:13]#[N:14])[NH:6][C:5]2=[O:15].[Cl:16][C:17]1[C:18]([CH3:27])=[C:19]([S:23](Cl)(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=1>N1C=CC=CC=1>[Cl:16][C:17]1[C:18]([CH3:27])=[C:19]([S:23]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH2:11][CH2:12][C:13]#[N:14])[NH:6][C:5]3=[O:15])(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 68835059HCID 68835059, compound

Product 1

HCID 68834598HCID 68834598, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(5-amino-3-oxo-2,3-dihydro-indazol-1-yl)-propionitrile (0.08 g) in pyridine (1 mL) was added 3-chloro-2-methylbenzenesulfonylchoride (0.089 g) in one go. The solution was stirred at 60° C. for 24 hours. The pyridine was then removed in vacuo and the residue was dissolved in EtOAc/water and separated. The aqueous phase was extracted a further two times with EtOAc and the combined organic phases were washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the volatiles were removed in vacuo to afford a crude residue. The crude material was purified via flash column chromatography eluting with EtOAc/nHeptane/1% AcOH) to afford the desired 3-Chloro-N-[1-(2-cyano-ethyl)-3-oxo-2,3-dihydro-1H-indazol-5-yl]-2-methyl-benzenesulfonamide (0.087 g) as a light brown solid. MS (ESI+): 391.0 [M+H]+).

Workup

  1. customThe pyridine was then removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc/water
  3. customseparated
  4. extractionThe aqueous phase was extracted a further two times with EtOAc
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe drying agent was removed by filtration
  8. customthe volatiles were removed in vacuo
  9. customto afford a crude residue
  10. customThe crude material was purified via flash column chromatography
  11. washeluting with EtOAc/nHeptane/1% AcOH)

Sources & evidence

ORD record
ord-cd129ff2804c498aba75e8c4630f1eca
Source dataset
uspto-grants-2009_05
Patent number
US07528158B2

Reaction notes

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