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Sodium hydride → HCID 46830921, Verbindung

HRID 1848345
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1848345
[OH:1][CH2:2][C:3]1([C:6]2[N:24]=[C:9]3[C:10]([O:22][CH3:23])=[CH:11][CH:12]=[C:13]([C:14]4[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=4)[C:17]#[N:18])[N:8]3[N:7]=2)[CH2:5][CH2:4]1.[H-].[Na+].[N:27]1([C:32](Cl)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]1.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[C:17]([C:16]1[CH:15]=[C:14]([C:13]2[N:8]3[N:7]=[C:6]([C:3]4([CH2:2][O:1][C:32]([N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)=[O:33])[CH2:5][CH2:4]4)[N:24]=[C:9]3[C:10]([O:22][CH3:23])=[CH:11][CH:12]=2)[CH:21]=[CH:20][CH:19]=1)#[N:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 709371-Pyrrolidinecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 46830920HCID 46830920, Verbindung2×

Produkt 1

HCID 46830921HCID 46830921, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under an argon atmosphere 3-[2-(1-Hydroxymethyl-cyclopropyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzonitrile (compound 150) (0.03 g, 0.08 mmol) was dissolved in DMF (0.5 mL). NaH (0.02 g, 0.48 mmol) was added and the suspension was heated at 65° C. for 1 h after which 1-pyrrolidine carbonylchloride (0.088 mL, 0.8 mmol) was added. Stirring was performed at 65° C. for 1 h. The reaction mixture was cooled and aq. NaHCO3 and H2O was added. The aqueous phase was extracted with EtOAc (×2). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica using DCM:MeOH 99:1 as eluent to afford the title compound as a solid.

Aufarbeitung

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. extractionThe aqueous phase was extracted with EtOAc (×2)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-b2d2baa632684bac88e7e650bc8f59c0
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08952162B2

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