Ethyl Acetate → (R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamide

HRID 2201087

Reaktionsgleichung

Reaktionsgleichung von HRID 2201087
Cl.[NH2:2][C@H:3]([CH2:7][CH3:8])[C:4]([NH2:6])=[O:5].[Cl:9][C:10]1[C:15]([C:16]#[N:17])=[CH:14][C:13]([F:18])=[C:12](Cl)[N:11]=1.CCN(C(C)C)C(C)C.CCOC(C)=O>CN1C(=O)CCC1>[Cl:9][C:10]1[N:11]=[C:12]([NH:2][C@H:3]([CH2:7][CH3:8])[C:4]([NH2:6])=[O:5])[C:13]([F:18])=[CH:14][C:15]=1[C:16]#[N:17]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 16218339(2R)-2-aminobutanamide hydrochloride

Produkt 1

HCID 86666160(R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamideAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To the mixture of (R)-(−)-2-aminobutanamide hydrochloride (1.00 g, 7.2 mmol) and 2,6-dichloro-5-fluoro-3-pyridinecarbonitrile (0.92 g, 4.8 mmol) in 40 mL NMP added DIEA (2.5 mL, 14.4 mmol). The mixture was then sent to 100° C. for stirring for 1 h. The mixture was cooled to RT, and to it was poured 300 mL EtOAc. The mixture was washed with brine four times. The organic phase was dried, concentrated and purified using silica flash column (70% EtOAc-30% DCM) to isolate (R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamide (1.21 g, 98% yield).

Aufarbeitung

  1. customwas then sent to 100° C.
  2. washThe mixture was washed with brine four times
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-b54ef00c6f0e484a94626fc0ab96e84e
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359375B2

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