Ethanesulfonyl chloride → N-(4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)-N-(ethylsulfonyl)ethanesulfonamide

HRID 632743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 632743
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=2[F:37])=[C:6]([C:8]2[C:9]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1.[CH2:38]([S:40](Cl)(=[O:42])=[O:41])[CH3:39]>ClCCl>[F:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[O:29][C:5]1[CH:4]=[CH:3][C:2]([N:1]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[S:40]([CH2:38][CH3:39])(=[O:42])=[O:41])=[CH:7][C:6]=1[C:8]1[C:9]2[CH:18]=[CH:17][N:16]([S:19]([C:22]3[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=3)(=[O:20])=[O:21])[C:10]=2[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=1

Komponenten

4

Edukt 2

HCID 11667Ethanesulfonyl chlorideHCID 89657311HCID 89657311, Verbindung

Produkt 1

HCID 89657386N-(4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)-N-(ethylsulfonyl)ethanesulfonamideAusbeute 181,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-(5-amino-2-(2,4-difluorophenoxy)phenyl)-6-methyl-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (4.35 g, 8.34 mmol) in dichloromethane (50 mL) was cooled to 0° C. To this solution was added ethanesulfonyl chloride (2.37 mL, 25.0 mmol). The reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated, and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 80% ethyl acetate/hexanes) to provide N-(4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)-N-(ethylsulfonyl)ethanesulfonamide (5.34 g, 91% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with additional ethyl acetate twice
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (silica gel, 80% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9d37f97e08c8458181174fb6c30dd0a8
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321765B2

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