Ethyl bromoacetate → Ethyl N-[2-{[2,2-bis(methyloxy)ethyl]amino}-6-(methyloxy)-3-pyridinyl]glycinate

HRID 657102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657102
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][NH:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([O:13][CH3:14])[N:7]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C=O)C>[CH3:16][O:15][CH:3]([O:2][CH3:1])[CH2:4][NH:5][C:6]1[C:11]([NH:12][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10][CH:9]=[C:8]([O:13][CH3:14])[N:7]=1

Komponenten

6

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 86635355N2-[2,2-Bis(methyloxy)ethyl]-6-(methyloxy)-2,3-pyridinediamine

Produkt 1

HCID 68811995Ethyl N-[2-{[2,2-bis(methyloxy)ethyl]amino}-6-(methyloxy)-3-pyridinyl]glycinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of N2-[2,2-bis(methyloxy)ethyl]-6-(methyloxy)-2,3-pyridinediamine (2.2 g, 10 mmol), ethyl bromoacetate (1.1 mL, 1.65 g, 10 mmol) and potassium carbonate (2.1 g, 20 mmol) in acetonitrile (50 mL) and DMF (5 mL) was stirred at room temperature overnight. The mixture was filtered and evaporated. The residue was dissolved in ethyl acetate and washed with water and brine. The organic extract was concentrated and added to a silica column which was then eluted with 0-100% ethyl acetate in hexane affording product (2.5 g, 82%).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. extractionThe organic extract
  6. concentrationwas concentrated
  7. additionadded to a silica column which
  8. washwas then eluted with 0-100% ethyl acetate in hexane affording product (2.5 g, 82%)

Quellen und Nachweise

ORD-Eintrag
ord-c9089bf87fd34a388c34d7ae86ad33e5
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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