7-Aminoindole → HCID 11100239, compound

HRID 1107443

Reaction equation

HRID 1107443 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[S:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)(=[O:14])(=[O:13])[NH2:12]>N1C=CC=CC=1>[NH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][S:21]([C:18]2[CH:17]=[CH:16][C:15]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:20][CH:19]=2)(=[O:23])=[O:22])[CH:7]=[CH:8]1

Participants

4

Reactant 2

HCID 1116347-AminoindoleHCID 109561594-Sulfamoylbenzene-1-sulfonyl chloride

Product 1

HCID 11100239HCID 11100239, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The synthesis of the present compound can be carried out according to the process disclosed in JP-A-7-165708. For example, the present compound can be synthesized as follows. After dissolving 264 mg (2 mmol) of 7-amino-1H-indole in pyridine, 767 mg (3 mmol) of 4-sulfamoylbenzenesulfonyl chloride is added thereto under stirring at room temperature. After the mixture is stirred overnight at room temperature, the solvent is evaporated under reduced pressure. Ethyl acetate and 0.2 N hydrochloric acid are added to the resulting residue. The organic layer is separated, washed with water, and dried over magnesium sulfate, followed by evaporation of the solvent. The resulting residue is purified by silica gel column chromatography to give 445 mg of N-(1H-indol-7-yl)-4-sulfamoylbenzenesulfonamide.

Workup

  1. customThe synthesis of the present compound
  2. additionis added
  3. stirringAfter the mixture is stirred overnight at room temperature
  4. customthe solvent is evaporated under reduced pressure
  5. additionEthyl acetate and 0.2 N hydrochloric acid are added to the resulting residue
  6. customThe organic layer is separated
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. customfollowed by evaporation of the solvent
  10. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-43a8760c721b4de49c9f488aa7441b9f
Source dataset
uspto-grants-2000_05
Patent number
US06060498

Linked notes

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