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Nicotinoyl chloride → N-{3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-nicotinamide

HRID 60110
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Reaktionsgleichung

Reaktionsgleichung von HRID 60110
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([NH:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=3)[CH:9]=[C:4]2[CH:3]=[CH:2]1.[Cl-].[Cl-].[Cl-].[Al+3].[F:23][C:24]1[C:32]([NH:33][S:34]([CH2:37][CH2:38][CH3:39])(=[O:36])=[O:35])=[CH:31][CH:30]=[C:29]([F:40])[C:25]=1[C:26](Cl)=[O:27].C(Cl)(=O)C1C=CC=NC=1>ClCCl.O.O1CCCC1.C(N(CC)CC)C>[F:23][C:24]1[C:32]([NH:33][S:34]([CH2:37][CH2:38][CH3:39])(=[O:35])=[O:36])=[CH:31][CH:30]=[C:29]([F:40])[C:25]=1[C:26]([C:3]1[C:4]2[C:5](=[N:6][CH:7]=[C:8]([NH:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=3)[CH:9]=2)[NH:1][CH:2]=1)=[O:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 82604Nicotinoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 580868612,6-Difluoro-3-(propane-1-sulfonylamino)-benzoyl chlorideHCID 58368850N-(1H-pyrrolo[2,3-b]pyridin-5-yl)-nicotinamide

Produkt 1

HCID 53261721N-{3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

In a reaction vial, N-(1H-pyrrolo[2,3-b]pyridin-5-yl)-nicotinamide (37, 0.050 g, 0.21 mmol) is dissolved in 2 mL of dichloromethane. Aluminum trichloride (0.1 g, 1 mmol) and 2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl chloride (38, 0.075 g, 0.25 mmol) are added in one portion, and the reaction is stirred at room temperature for 36 hours, then diluted with water and extracted 3× with ethyl acetate. The organic layers are combined and washed 2× with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The amide linked at the 5-position is lost, so half the material is mixed with 3 mL of triethylamine in 2 mL of tetrahydrofuran and nicotinoyl chloride (36, 0.036 g, 0.25 mmol) is added and stirred at room temperature overnight. The reaction is diluted with water and extracted 3× with ethyl acetate. The organic layers are combined and washed 2× with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is further purified by reverse phase chromatography and the resulting material confirmed by LC-MS.

Aufarbeitung

  1. extractionextracted 3× with ethyl acetate
  2. washwashed 2× with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. additionis added
  7. stirringstirred at room temperature overnight
  8. extractionextracted 3× with ethyl acetate
  9. washwashed 2× with brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated under vacuum
  13. customThe resulting material is further purified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-85fa2634a78c4b4f9fce70bf9e55d550
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09440969B2

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