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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluoro-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide

HRID 2196741
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2196741
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH:22]1[C:26]2=[N:27][CH:28]=[C:29]([NH2:31])[CH:30]=[C:25]2[CH:24]=[CH:23]1.[CH2:32]([N:34]([C:40]1[C:41]([F:50])=[C:42]([C:46]([F:49])=[CH:47][CH:48]=1)[C:43](O)=[O:44])[S:35](=[O:39])(=[O:38])[NH:36][CH3:37])[CH3:33]>CN(C=O)C.CCOC(C)=O>[CH2:32]([N:34]([C:40]1[C:41]([F:50])=[C:42]([C:46]([F:49])=[CH:47][CH:48]=1)[C:43]([NH:31][C:29]1[CH:30]=[C:25]2[CH:24]=[CH:23][NH:22][C:26]2=[N:27][CH:28]=1)=[O:44])[S:35](=[O:38])(=[O:39])[NH:36][CH3:37])[CH3:33]
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Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 117151871H-pyrrolo(2,3-b)pyridin-5-amineHCID 670525023-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoic acid

Produkt 1

HCID 671564383-(N-ethyl-N-methylsulfamoylamino)-2,6-difluoro-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamideAusbeute 7,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

HOBt (0.011 g, 0.085 mmol), EDCI (0.036 g, 0.19 mmol), and 1H-pyrrolo[2,3-b]pyridin-5-amine (0.025 g, 0.19 mmol) was added to 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoic acid (0.050 g, 0.17 mmol) in DMF (1 mL). The reaction mixture was stirred at room temperature for 16 hours. The mixture was diluted with EtOAc (6 mL) and washed with brine (3×5 mL). The organic layers were dried over sodium sulfate, decanted, and concentrated under reduced pressure. The residue was purified via silica gel chromatography eluting with 5% MeOH-DCM to afford 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluoro-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (0.005 g, 0.012 mmol, 7.2% yield). m/z (APCI-neg) M−1=408.0.

Aufarbeitung

  1. washwashed with brine (3×5 mL)
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. customdecanted
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with 5% MeOH-DCM

Quellen und Nachweise

ORD-Eintrag
ord-46cad1514c254d8ba3ef4bd1d5243730
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08338452B2

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