Trifluoroacetic acid → N-(6-Hydroxyimidazo[1,2-A]pyridin-2-YL)cyclopropanecarboxamide

HRID 2095836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095836
COC1C=CC(C[O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH:15]=[C:16]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[N:17]=3)[CH:14]=2)=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>FC(C1C=CC=CC=1)(F)F>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([CH:15]=[C:16]([NH:18][C:19]([CH:21]3[CH2:22][CH2:23]3)=[O:20])[N:17]=2)[CH:14]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 58158646N-(6-((4-Methoxybenzyl)oxy)imidazo[1,2-A]pyridin-2-YL)cyclopropanecarboxamide

Produkt 1

HCID 58158532N-(6-Hydroxyimidazo[1,2-A]pyridin-2-YL)cyclopropanecarboxamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7368(Trifluoromethyl)benzeneLösungsmittel

Versuchsvorschrift

To a solution of N-{6-[(4-methoxybenzyl)oxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide (10.1 g, 29.9 mmol) and anisole (25.97 mL, 239.2 mmol) in trifluoromethylbenzene (200 mL) was added trifluoroacetic acid (40.4 mL), and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted 5 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was washed with ethyl acetate and collected by filtration to give the title compound (5.7 g, 88%) as a pale-brown solid.

Aufarbeitung

  1. extractionthe mixture was extracted 5 times with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washThe obtained residue was washed with ethyl acetate
  7. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e7b431dde53340de96cf9479a5816ad9
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445509B2

Notizen zur Reaktion

Wird geladen…