Methanol → N-[5-(5-amino-2-chloro-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]acetamide

HRID 1800543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1800543
[BH4-].[Na+].CO.[C:5]([NH:8][C:9]1[S:10][C:11]2[C:16]([N:17]=1)=[CH:15][CH:14]=[C:13]([O:18][C:19]1[C:20]([Cl:33])=[CH:21][C:22]([F:32])=[C:23]([NH:25]C(=O)C(F)(F)F)[CH:24]=1)[N:12]=2)(=[O:7])[CH3:6].O>C(O)C>[NH2:25][C:23]1[C:22]([F:32])=[CH:21][C:20]([Cl:33])=[C:19]([CH:24]=1)[O:18][C:13]1[N:12]=[C:11]2[S:10][C:9]([NH:8][C:5](=[O:7])[CH3:6])=[N:17][C:16]2=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86646020N-(5-{[2-(acetylamino) [1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-4-chloro-2-fluorophenyl)-2,2,2-trifluoroacetamide

Produkt 1

HCID 86646021N-[5-(5-amino-2-chloro-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]acetamideAusbeute 192,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of sodium borohydride (3.38 g, 100 mmol) in ethanol (60 mL) was added dropwise methanol (40 mL) under ice-cooling, and N-(5-{[2-(acetylamino) [1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-4-chloro-2-fluorophenyl)-2,2,2-trifluoroacetamide (2.16 g, 4.81 mmol) was added in portions thereto under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr, and poured into water (400 mL), and the mixture was extracted with ethyl acetate (200 mL×2). The ethyl acetate layers were combined, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with diethyl ether, collected by filtration, and dried under reduced pressure to give the title compound (3.26 g, 68%) as white powder crystals.

Aufarbeitung

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. extractionthe mixture was extracted with ethyl acetate (200 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washThe obtained residue was washed with diethyl ether
  8. filtrationcollected by filtration
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-69ebd5c52a8748cbb9c08a15841369c7
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344135B2

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