Water → HCID 178474433, Verbindung

HRID 241453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241453
Br[CH:2]([CH3:14])[C:3]([C:5]1[CH:6]=[N:7][C:8]([CH:11]([F:13])[F:12])=[CH:9][CH:10]=1)=O.[C:15]([NH:18][C:19]([NH2:21])=[NH:20])(=[O:17])[CH3:16].O>CN(C=O)C>[F:12][CH:11]([F:13])[C:8]1[N:7]=[CH:6][C:5]([C:3]2[NH:21][C:19]([NH:18][C:15](=[O:17])[CH3:16])=[N:20][C:2]=2[CH3:14])=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 866742042-Bromo-1-[6-(difluoromethyl)-3-pyridyl]propan-1-oneHCID 178475102HCID 178475102, Verbindung

Produkt 1

HCID 178474433HCID 178474433, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Dissolve 2-bromo-1-[6-(difluoromethyl)-3-pyridyl]propan-1-one (0.500 g, 1.89 mmol) and acetyl guanidine (0.514 g, 5.68 mmol) in DMF (12 mL). Heat the mixture to 50° C., and stir for 16 hours. Pour the mixture into water, and extract with EtOAc (3×20 mL). Dry the combined organic extracts over sodium sulfate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify the resulting residue by flash chromatography (silca gel) eluting with a 40:1 ratio of DCM/MeOH to give the title compound as a white solid (0.229 g, 46% yield). LCMS (m/z) 267 (M+1).

Aufarbeitung

  1. extractionextract with EtOAc (3×20 mL)
  2. dry with materialDry the combined organic extracts over sodium sulfate
  3. filtrationfilter
  4. customcollect the filtrate
  5. concentrationand concentrate the filtrate under reduced pressure
  6. customPurify the resulting residue by flash chromatography (silca gel)
  7. washeluting with a 40:1 ratio of DCM/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-266aacee16f84e04829bd18de27c27d4
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648200B2

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