Benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)amide → Benzo[b]thiophene-2-sulfonic acid [2-(5-(1,1-dichloro-2,2,2-trifluoroethyl)-2-methoxy-benzenesulfonylamino)phenyl]-amide

HRID 730227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730227
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1)(=[O:11])=[O:10].[Cl:21][C:22]([C:28]1[CH:29]=[CH:30][C:31]([O:38][CH3:39])=[C:32]([S:34](Cl)(=[O:36])=[O:35])[CH:33]=1)([Cl:27])[C:23]([F:26])([F:25])[F:24]>C(Cl)Cl.N1C=CC=CC=1>[Cl:21][C:22]([C:28]1[CH:29]=[CH:30][C:31]([O:38][CH3:39])=[C:32]([S:34]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][S:9]([C:12]2[S:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[CH:13]=2)(=[O:11])=[O:10])(=[O:36])=[O:35])[CH:33]=1)([Cl:27])[C:23]([F:26])([F:25])[F:24]

Komponenten

5

Edukt 2

HCID 86240018Benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)amideHCID 866050465-(1,1-Dichloro-2,2,2-trifluoroethyl)-2-methoxybenzenesulfonyl chloride

Produkt 1

HCID 11671771Benzo[b]thiophene-2-sulfonic acid [2-(5-(1,1-dichloro-2,2,2-trifluoroethyl)-2-methoxy-benzenesulfonylamino)phenyl]-amideAusbeute 59,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)-amide (1 mmol, prepared as in Example 1) in DCM (2 mL) and pyridine (2 mL), 5-(1,1-dichloro-2,2,2-trifluoroethyl)-2-methoxybenzenesulfonyl chloride (1.1 mmol) was added at RT and the reaction mixture was then allowed to stir at RT overnight. The reaction mixture was then diluted with DCM (20 mL). The organic phase was washed with 10% aqueous HCl (20 mL), water (20 mL) and brine (20 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to afford 374 mg of benzo[b]thiophene-2-sulfonic acid [2-(5-(1,1-dichloro-2,2,2-trifluoroethyl)-2-methoxy-benzenesulfonylamino)phenyl]-amide. LC: Tr 1.40 min; MS: 625.8 (M+1).

Aufarbeitung

  1. washThe organic phase was washed with 10% aqueous HCl (20 mL), water (20 mL) and brine (20 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by flash column chromatography
  6. washeluting with DCM/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-6a0e6262dc064317b7b51175b1e1e127
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582673B2

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