Hydrochloric Acid → N-(2-methylcyclopentyl)-3-fluoro-4-(2-propynyloxy)benzamide

HRID 602001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602001
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12](F)=[C:11]([F:16])[CH:10]=1.[CH2:18]([OH:21])[C:19]#[CH:20].[H-].[Na+].Cl>CN(C=O)C>[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([O:21][CH2:18][C:19]#[CH:20])=[C:11]([F:16])[CH:10]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 57445707N-(2-methylcyclopentyl)-3,4-difluorobenzamide

Produkt 1

HCID 57445708N-(2-methylcyclopentyl)-3-fluoro-4-(2-propynyloxy)benzamideAusbeute 41,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 2 ml of DMF were added 0.23 g of N-(2-methylcyclopentyl)-3,4-difluorobenzamide and 0.11 g of propargyl alcohol. To the mixture obtained was added 60 mg of 60% sodium hydride (oily) at 0° C. The mixture was stirred at room temperature for 2 hours. Then, dilute hydrochloric acid was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with brine, dried on magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.11 g of N-(2-methylcyclopentyl)-3-fluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 69 of the present invention) represented by the formula:

Aufarbeitung

  1. customTo the mixture obtained
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried on magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1bf7884cf91144649307f95aa87047ab
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902400B2

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