Imidazole → HCID 22228569, compound

HRID 1173111Notes

Reaction equation

HRID 1173111 reaction equation
Br[CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:26]=2[NH:25][CH:24]=[C:23]3[Cl:27])(=[O:16])=[O:15])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1>CN(C)C=O>[Cl:27][C:23]1[C:22]2[C:26](=[C:18]([NH:17][S:14]([C:11]3[CH:12]=[CH:13][C:8]([S:5](=[O:7])(=[O:6])[NH:4][CH2:3][CH2:2][N:28]4[CH:32]=[CH:31][N:30]=[CH:29]4)=[CH:9][CH:10]=3)(=[O:16])=[O:15])[CH:19]=[CH:20][CH:21]=2)[NH:25][CH:24]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 22228549HCID 22228549, compound

Product 1

HCID 22228569HCID 22228569, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

557 mg (1.13 mmol) of 4-[N-(2-bromoethyl)sulfamoyl]-N-(3-chloro-1H-indole-7-yl)benzenesulfonamide and 820 mg (12.0 mmol) of imidazole were added to 10 ml of dimethylformamide and the mixture was stirred at 80° C. for 2 days. After concentrating, the residue was dissolved in ethyl acetate. The mixture was washed with water, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography, to give 324 mg of the title compound.

Workup

  1. concentrationAfter concentrating
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe mixture was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cb29c47aa73e4251832cd9134e7fd5bd
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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