Ethoxyacetyl chloride → N-(2-chloro-4-{[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]amino}-5,6-dimethylpyridin-3-yl)-2-ethoxyacetamide

HRID 1469310

Reaktionsgleichung

Reaktionsgleichung von HRID 1469310
[CH2:1]([O:3][CH2:4][C:5](Cl)=[O:6])[CH3:2].[NH2:8][C:9]1[C:10]([Cl:26])=[N:11][C:12]([CH3:25])=[C:13]([CH3:24])[C:14]=1[NH:15][CH2:16][C:17]1([OH:23])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>ClCCl>[Cl:26][C:10]1[C:9]([NH:8][C:5](=[O:6])[CH2:4][O:3][CH2:1][CH3:2])=[C:14]([NH:15][CH2:16][C:17]2([OH:23])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:13]([CH3:24])=[C:12]([CH3:25])[N:11]=1

Komponenten

4

Edukt 2

HCID 84189Ethoxyacetyl chloride2×HCID 575155244-{[(3-amino-2-chloro-5,6-dimethylpyridin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol

Produkt 1

HCID 57515525N-(2-chloro-4-{[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]amino}-5,6-dimethylpyridin-3-yl)-2-ethoxyacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere ethoxyacetyl chloride (2.26 g, 16.6 mmol) was added dropwise to a chilled (0° C.) suspension of 4-{[(3-amino-2-chloro-5,6-dimethylpyridin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol (3.96 g) in dichloromethane (140 mL). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was cooled to 0° C., more ethoxyacetyl chloride (0.3 mL) was added, and the reaction mixture was stirred at ambient temperature for an additional 4 hours. The reaction mixture was concentrated under reduced pressure to provide crude N-(2-chloro-4-{[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]amino}-5,6-dimethylpyridin-3-yl)-2-ethoxyacetamide.

Aufarbeitung

  1. temperaturea chilled
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. stirringthe reaction mixture was stirred at ambient temperature for an additional 4 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ed8977e476b8468a92244989e20ce5b1
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006264B2

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