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Acetic Anhydride → N-(5-{(1E)-3-Oxo-3-[3-(pyridin-4-ylmethoxy)azetidin-1-yl]prop-1-en-1-yl}pyridin-2-yl)acetamide

HRID 82970
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 82970
[O:1]=[C:2]([N:12]1[CH2:15][CH:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH2:13]1)/[CH:3]=[CH:4]/[C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[N:9][CH:10]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25].C([O-])(O)=O.[Na+]>C1COCC1>[O:1]=[C:2]([N:12]1[CH2:13][CH:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[CH2:15]1)/[CH:3]=[CH:4]/[C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:24](=[O:26])[CH3:25])=[N:9][CH:10]=1
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Komponenten

5

Edukt 3

HCID 7918Acetic Anhydride2×HCID 516892Sodium Bicarbonate2×HCID 529505295-{(1E)-3-Oxo-3-[3-(pyridin-4-ylmethoxy)azetidin-1-yl]prop-1-en-1-yl}pyridin-2-amine

Produkt 1

HCID 52950530N-(5-{(1E)-3-Oxo-3-[3-(pyridin-4-ylmethoxy)azetidin-1-yl]prop-1-en-1-yl}pyridin-2-yl)acetamideAusbeute 13,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 5-{(1E)-3-oxo-3-[3-(pyridin-4-ylmethoxy)azetidin-1-yl]prop-1-en-1-yl}pyridin-2-amine (16 mg, 0.05 mmol) and acetic anhydride (6 μL, 0.06 mmol) in THF (2.4 mL) was added NaHCO3 (5.5 mg, 0.065 mmol). The reaction mixture was warmed at 60° C. and stirred for 40 h. LCMS showed that some starting material was remaining. Another portion of acetic anhydride (6 μL) and NaHCO3 (5.5 mg) were added and the mixture was stirred at 60° C. for 24 h. These additions were repeated twice over 48 h. The mixture was then concentrated, partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under vacuum to give an oil. The crude was purified on preparative TLC (eluent: 90/10 DCM/MeOH) to give the title compound (2.3 mg, 12%) as a pale yellow solid.

Aufarbeitung

  1. stirringthe mixture was stirred at 60° C. for 24 h
  2. waitThese additions were repeated twice over 48 h
  3. concentrationThe mixture was then concentrated
  4. custompartitioned between water and ethyl acetate
  5. extractionThe aqueous layer was extracted twice with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customto give an oil
  11. customThe crude was purified on preparative TLC (eluent: 90/10 DCM/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-a873a3a3e63847f290f09aae548c67b1
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846711B2

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