2,6-Diaminopyridine → N-(6-Amino-pyridin-2-yl)-2-(2-methoxy-ethoxy)-acetamide

HRID 1787708

Reaktionsgleichung

Reaktionsgleichung von HRID 1787708
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([OH:9])=O.ClC(OCC(C)C)=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[N:20]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.C(N(CC)CC)C>[NH2:18][C:19]1[N:20]=[C:21]([NH:25][C:7](=[O:9])[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:22]=[CH:23][CH:24]=1

Komponenten

7

Edukt 4

HCID 88612,6-DiaminopyridineHCID 27642(2-Methoxyethoxy)acetic acidHCID 62365Isobutyl chloroformateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 57600508N-(6-Amino-pyridin-2-yl)-2-(2-methoxy-ethoxy)-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4.9 ml of (2-methoxyethoxy)-acetic acid is dissolved in 500 ml of tetrahydrofuran. 9.7 ml of triethylamine and 5.6 ml of isobutyl chloroformate are added at 0° C., and it is stirred for 30 minutes at 0° C. 3.96 g of 2,6-diaminopyridine is added, and it is stirred for another 4 hours at room temperature. The reaction mixture is mixed with semi-saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic solution is washed with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation, and after purification by chromatography on silica gel, 5.04 g of the title compound is obtained.

Aufarbeitung

  1. stirringit is stirred for another 4 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic solution is washed with saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customafter purification by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1dda6433de5b4aab9845db9fde330951
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511059B2

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