Water → 5-(1-Dimethylsulfamoyl-1H-imidazol-2-yl)-7-fluoro-3-[(E)-2-(4-fluorophenyl)-vinyl]-indazole-1-sulfonic Acid Dimethylamide

HRID 34092Notes

Reaction equation

HRID 34092 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[C:7]2/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1.[H-].[Na+].[CH3:27][N:28]([CH3:33])[S:29](Cl)(=[O:31])=[O:30].[OH2:34]>CN(C)C=O>[CH3:27][N:28]([CH3:33])[S:29]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([C:20]3[N:24]([S:29](=[O:30])(=[O:34])[N:28]([CH3:33])[CH3:27])[CH:23]=[CH:22][N:21]=3)=[CH:3][C:2]=2[F:1])[C:7](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[N:8]1)(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 178505671HCID 178505671, compound

Product 1

HCID 600346195-(1-Dimethylsulfamoyl-1H-imidazol-2-yl)-7-fluoro-3-[(E)-2-(4-fluorophenyl)-vinyl]-indazole-1-sulfonic Acid Dimethylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

36.5 mg of 7-fluoro-3-[(E)-2-(4-fluorophenyl)-vinyl]-5-(1H-imidazol-2-yl)-1H-indazole obtained by Example 603 was dissolved in N,N-dimethylformamide, and added with 14 mg of sodium hydride (containing 60%) under ice cooling and stirred for 10 minutes. Adding dropwise with 30.3 μl of N,N-dimethylsulfamoyl chloride, the solution was warmed to room temperature and stirred overnight. After stopping the reaction by adding water, the solution was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine. After drying the organic layer over magnesium sulfate, the solvent was evaporated. The crude product was purified by preparative TLC, to afford 14.2 mg of the title compound.

Workup

  1. stirringstirred overnight
  2. customthe reaction
  3. extractionthe solution was extracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated brine
  5. dry with materialAfter drying the organic layer over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-6cd894b58e92460fbc68cfe887bbe585
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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