2,3-Dichlorobenzene-1-sulfonyl chloride → HCID 11692400, compound

HRID 2110274Notes

Reaction equation

HRID 2110274 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([NH:18][C:19]([C:21]4[CH:25]=[CH:24][S:23][CH:22]=4)=[O:20])=[N:14][NH:15]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Cl:26][C:27]1[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=1[S:34](Cl)(=[O:36])=[O:35]>N1C=CC=CC=1.ClCCl>[Cl:26][C:27]1[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=1[S:34]([NH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([NH:18][C:19]([C:21]4[CH:25]=[CH:24][S:23][CH:22]=4)=[O:20])=[N:14][NH:15]3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)(=[O:36])=[O:35]

Participants

5

Reactant 2

HCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 68854066HCID 68854066, compound

Product 1

HCID 11692400HCID 11692400, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 1.72 g of 6-(4-aminophenyl)-3-[(thiophen-3-yl)carbonylamino]-1H-indazole hydrochloride in 69 mL of pyridine is admixed at 0° C. with a solution of 1.14 g of 2,3-dichlorobenzenesulfonyl chloride in 23 mL of dichloromethane. The reaction mixture is stirred for 3 hours at a temperature in the region of 20° C. and then concentrated under reduced pressure. The dry residue is diluted in ethyl acetate, washed with water and then washed with saturated sodium chloride solution and concentrated under reduced pressure. The foam obtained is purified by flash chromatography, eluting with a dichloromethane/methanol/acetonitrile (96/2/2 by volume) mixture, to give 0.69 g of 3-thiophenecarboxylic acid {6-[4-(2,3-dichlorobenzenesulfonylamino)phenyl]-1H-indazol-3-yl}amide, whose characteristics are as follows:

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe dry residue is diluted in ethyl acetate
  3. washwashed with water
  4. washwashed with saturated sodium chloride solution
  5. concentrationconcentrated under reduced pressure
  6. customThe foam obtained
  7. customis purified by flash chromatography
  8. washeluting with a dichloromethane/methanol/acetonitrile (96/2/2 by volume) mixture

Sources & evidence

ORD record
ord-967ca5d7f2fa401ba4efc3f99f0f19e8
Source dataset
uspto-grants-2009_04
Patent number
US07517902B2

Reaction notes

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