Tetronic acid → 4-[[(6-Chloro-5-fluoropyridin-3-yl)methyl](methyl)amino]furan-2(5h)-one

HRID 425751

Reaktionsgleichung

Reaktionsgleichung von HRID 425751
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=O.[Cl:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][NH:16][CH3:17])=[CH:11][C:10]=1[F:18]>C(O)(=O)C>[Cl:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:17])[C:2]2[CH2:4][O:5][C:6](=[O:7])[CH:1]=2)=[CH:11][C:10]=1[F:18]

Komponenten

4

Edukt 2

HCID 521261Tetronic acidHCID 86634700((6-Chloro-5-fluoropyridin-3-yl)methyl)(methyl)amine

Produkt 1

HCID 251910444-[[(6-Chloro-5-fluoropyridin-3-yl)methyl](methyl)amino]furan-2(5h)-oneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

24.80 g (248 mmol) of tetronic acid are added slowly to 41.40 g (225.3 mmol) of N-[(6-chloro-5-fluoropyridin-3-yl)methyl]methanamine (III-1) in 64 ml of acetic acid, and the mixture is stirred at room temperature for about 16 hours. The reaction mixture is concentrated under reduced pressure, the residue is taken up in ethyl acetate and the mixture is washed successively twice with 1 N aqueous hydrochloric acid, twice with 1 N aqueous sodium hydroxide solution and saturated sodium chloride solution and dried over sodium sulphate. Concentration of the organic phase under reduced pressure and purification of the residue by recrystallization from ethyl acetate gives 30.0 g (52% of theory) of 4-[[(6-chloro-5-fluoropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. washthe mixture is washed successively twice with 1 N aqueous hydrochloric acid, twice with 1 N aqueous sodium hydroxide solution and saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customConcentration of the organic phase under reduced pressure and purification of the residue
  5. customby recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-441e1f78251b4448b30cb41ca5474081
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106212B2

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