6-((6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-5,7-difluoroquinoline → 1-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

HRID 1959762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959762
C([O:3][C:4]([C:6]1[N:11]=[C:10]2[N:12]([CH2:15][C:16]3[C:17]([F:27])=[C:18]4[C:23](=[CH:24][C:25]=3[F:26])[N:22]=[CH:21][CH:20]=[CH:19]4)[N:13]=[N:14][C:9]2=[N:8][CH:7]=1)=[CH2:5])C>C(O)(=O)C.Cl>[F:27][C:17]1[C:16]([CH2:15][N:12]2[C:10]3=[N:11][C:6]([C:4](=[O:3])[CH3:5])=[CH:7][N:8]=[C:9]3[N:14]=[N:13]2)=[C:25]([F:26])[CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[N:22]2

Komponenten

4

Edukt 1

HCID 698109656-((6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-5,7-difluoroquinoline

Produkt 1

HCID 698122851-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanoneAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To a solution of the 6-((6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-5,7-difluoroquinoline (6.0 mg, 0.45 mmol) in acetic acid, 3N HCl (0.1 mL) was added. The solution stirred at it for 2 h. Solvents were removed under reduced pressure. The residue was diluted with water, treated with aqueous NaHCO3 solution, extracted with DCM. The organic layer was washed sequentially with NaHCO3 (aq.) and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography with Hexane:ethyl acetate to give yellow solid 1-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (3.5 mg), yield 63%. LCMS (method B): [MH]+=340.9, tR=2.09 min.

Aufarbeitung

  1. customSolvents were removed under reduced pressure
  2. additionThe residue was diluted with water
  3. additiontreated with aqueous NaHCO3 solution
  4. extractionextracted with DCM
  5. washThe organic layer was washed sequentially with NaHCO3 (aq.) and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography with Hexane

Quellen und Nachweise

ORD-Eintrag
ord-f53875c05c3a47a384ad1476bc82b9ec
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410264B2

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