Water → HCID 59334933, compound

HRID 1517936Notes

Reaction equation

HRID 1517936 reaction equation
[CH2:1]([NH:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([NH:20][S:21]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)(=[O:23])=[O:22])=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41].O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([NH:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([N:20]([CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[S:21]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)(=[O:23])=[O:22])=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 59335041HCID 59335041, compound

Product 1

HCID 59334933HCID 59334933, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

150 mg 5-(3,5-dichloro-phenylsulphonylamino)-indole-1-carboxylic acid-benzylamide are dissolved in 5 ml dimethylformamide. 109 mg potassium carbonate and 51 μl tert.butyl bromoacetate are added thereto. The mixture is stirred for 4 hours at ambient temperature, the solvent is eliminated in vacuo and the residue is divided between water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried on magnesium sulphate. The solvents are eliminated in vacuo and the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 10:1 to 1:3).

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. customthe combined organic phases are dried on magnesium sulphate
  3. customthe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 10:1 to 1:3)

Sources & evidence

ORD record
ord-e7cdc965aec540cb805e36417885b0e4
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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