Hydrochloric Acid → N-[3-fluoro-6-(2-fluoro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095859
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[C:12]([NH:14][C:15]([CH:17]3[CH2:19][CH2:18]3)=[O:16])[N:13]=2)[CH:10]=1.O1CCCC1.OS(C(F)(F)[F:37])(=O)=O.FN1C(Cl)=CC=CC1Cl.Cl>C(#N)C.C(OCC)(=O)C>[F:37][C:11]1[N:9]2[CH:10]=[C:5]([O:4][C:3]3[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:2]=3[F:1])[CH:6]=[CH:7][C:8]2=[N:13][C:12]=1[NH:14][C:15]([CH:17]1[CH2:19][CH2:18]1)=[O:16]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 58158487N-[6-(2-fluoro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideHCID 866513971-Fluoro-2,6-dichloropyridine triflate

Produkt 1

HCID 58158450N-[3-fluoro-6-(2-fluoro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-[6-(2-fluoro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (121.6 mg, 0.341 mmol) in acetonitrile (0.5 mL)/tetrahydrofuran (0.5 mL) was added 1-fluoro-2,6-dichloropyridine triflate (129 mg, 0.409 mmol), and the mixture was stirred at room temperature for 2 hr. Tetrahydrofuran, ethyl acetate and 1N hydrochloric acid were added to the reaction mixture, and the mixture was extracted 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 purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=1/2→1/1) to give the title compound (15.2 mg, 12%) as a white solid.

Aufarbeitung

  1. extractionthe mixture was extracted 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. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=1/2→1/1)

Quellen und Nachweise

ORD-Eintrag
ord-becc1dc3cae245c3926562669af8fd1c
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445509B2

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