1-Propanesulfonyl chloride → N-(3-acetyl-1-(propylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzamide

HRID 2196693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196693
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2][CH3:3].[C:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([NH:20][C:21](=[O:37])[C:22]3[C:27]([F:28])=[CH:26][CH:25]=[C:24]([NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[C:23]=3[F:36])[CH:18]=2)[NH:13][CH:12]=1)(=[O:10])[CH3:9]>C(Cl)Cl>[C:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([NH:20][C:21](=[O:37])[C:22]3[C:27]([F:28])=[CH:26][CH:25]=[C:24]([N:29]([S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[C:23]=3[F:36])[CH:18]=2)[N:13]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[CH:12]=1)(=[O:10])[CH3:9]

Komponenten

4

Edukt 2

HCID 662791-Propanesulfonyl chlorideHCID 44223281N-(3-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide

Produkt 1

HCID 131730124N-(3-acetyl-1-(propylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzamideAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TEA (0.0163 mL, 0.117 mmol) and propane-1-sulfonyl chloride (0.00882 mL, 0.0779 mmol) were added to N-(3-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.195 mL, 0.0390 mmol) in DCM (0.4 mL). The solution was stirred at room temperature for 16 hours before concentration under reduced pressure. The resulting residue was purified via column chromatography (2% MeOH/DCM) to afford impure N-(3-acetyl-1-(propylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzamide (0.020 g, 0.0308 mmol, 79.1% yield).

Aufarbeitung

  1. customThe resulting residue was purified via column chromatography (2% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-bc74b8d3ff6c4d5b96853969155882e6
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338452B2

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