Water → HCID 86595214, compound

HRID 1793946Notes

Reaction equation

HRID 1793946 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH:11][S:12]([C:15]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:16]=1[O:23][CH3:24])(=[O:14])=[O:13].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C(N(CC)C(C)C)(C)C.O>CN(C)C=O>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][CH2:10][NH:11][S:12]([C:15]2[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:16]=2[O:23][CH3:24])(=[O:14])=[O:13])=[C:2]([NH:1][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 22219473HCID 22219473, compound

Product 1

HCID 86595214HCID 86595214, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 12.38 g of N-[2-(2-amino-4-bromo-phenyl)ethyl]-5-cyano-2-methoxybenzenesulfonamide, 3.68 mL of ethyl bromoacetate, and 7.88 mL of N,N-diisopropylethylamine in 100 mL of N,N-dimethylformamide was stirred at 55° C. for 16 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 7.38 g of ethyl [5-bromo-2-[2-(5-cyano-2-methoxybenzenesulfonylamino) ethyl]phenylamino]acetate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water, and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-1b3744791c9b4dcdb8e0856460fdf1d1
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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