2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → ethyl 5-amino-1-(oxan-4-yl)-1H-pyrazole-4-carboxylate

HRID 12883

Reaktionsgleichung

Reaktionsgleichung von HRID 12883
Cl.[O:2]1[CH2:7][CH2:6][CH:5]([NH:8][NH2:9])[CH2:4][CH2:3]1.C(O[CH:13]=[C:14]([C:20]#[N:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C.C([O-])(=O)C.[Na+]>C(O)C>[CH2:18]([O:17][C:15]([C:14]1[CH:13]=[N:9][N:8]([CH:5]2[CH2:6][CH2:7][O:2][CH2:3][CH2:4]2)[C:20]=1[NH2:21])=[O:16])[CH3:19]

Komponenten

5

Edukt 3

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 517045Sodium AcetateHCID 17773358(Oxan-4-yl)hydrazine hydrochloride

Produkt 1

HCID 67020774ethyl 5-amino-1-(oxan-4-yl)-1H-pyrazole-4-carboxylateAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
82.5 °C

Versuchsvorschrift

(Tetrahydro-pyran-4-yl)-hydrazine hydrochloride (1.975 g, 12.94 mmol), ethyl (ethoxymethylene)-cyanoacetate (1.958 g, 11.57 mmol) and sodium acetate (1.370 g; 16.70 mmol) were combined in ethanol (16 mL). The mixture was heated at 80-85° C. for 17 hours. After cooling to room temperature, the reaction was concentrated and the residue was partitioned between methylene chloride and water. The organic phase was separated and washed with water and then brine. Each aqueous phase was back extracted with methylene chloride. The two organic phases were combined, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography eluting with 60-100% ethyl acetate/hexanes to give 5-amino-1-(tetrahydro-pyran-4-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (2.554 g, 92%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction was concentrated
  3. customthe residue was partitioned between methylene chloride and water
  4. customThe organic phase was separated
  5. washwashed with water
  6. extractionEach aqueous phase was back extracted with methylene chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash chromatography
  10. washeluting with 60-100% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6f68aa42048a4899b155725c5423f581
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728029B2

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