Hydrazine → tert-butyl 3-amino-1H,4H,5H,6H,7H-pyrazolo(4,3-c)pyridine-5-carboxylate

HRID 550593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 550593
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](O)=[C:10]([C:15]#[N:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][NH2:18]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[NH:17][N:18]=[C:15]([NH2:16])[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 57447316HCID 57447316, Verbindung

Produkt 1

HCID 67201367tert-butyl 3-amino-1H,4H,5H,6H,7H-pyrazolo(4,3-c)pyridine-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 141.5 g of 3-cyano-4-hydroxy-1,2,5,6-tetrahydropyridine-1-carboxylic acid tert-butyl ester in 1.2 L of ethanol were added under stirring 57.8 mL of aqueous 35% hydrazine. The mixture was heated at 70° C. for 4 h. The solution was evaporated at under vacuum, the residue was diluted with 1 L of water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated to dryness. The crude product was taken-up with 300 mL tert-butyl methyl ether and the crystallized compound was collected by filtration to give 115.6 g of the title compound.

Aufarbeitung

  1. customThe solution was evaporated at under vacuum
  2. additionthe residue was diluted with 1 L of water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. filtrationthe crystallized compound was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-678ec52b602f41409abfe829c0503d8d
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947686B2

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