2-Methylpropanehydrazide → 5-Bromo-3-(5-isopropyl-[1,3,4]oxadiazol-2-yl)-pyridin-2-ylamine

HRID 632463

Reaktionsgleichung

Reaktionsgleichung von HRID 632463
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:12]([NH:17][NH2:18])(=O)[CH:13]([CH3:15])[CH3:14]>O=P(Cl)(Cl)Cl>[Br:11][C:8]1[CH:7]=[C:3]([C:4]2[O:6][C:12]([CH:13]([CH3:15])[CH3:14])=[N:17][N:18]=2)[C:2]([NH2:1])=[N:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 192392-MethylpropanehydrazideHCID 7374452-Amino-5-bromonicotinic acid

Produkt 1

HCID 902732895-Bromo-3-(5-isopropyl-[1,3,4]oxadiazol-2-yl)-pyridin-2-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-amino-5-bromo-nicotinic acid (1.0 g, 4.60 mmol) in POCl3 (20 mL) was added isobutyric acid hydrazide (705 mg, 6.912 mmol) at RT. The reaction temperature was slowly heated to 100° C. and stirred for 18 h. The solvent was evaporated under reduced pressure, the residue was basified with saturated cold sodium bicarbonate solution (50 mL), extracted with ethyl acetate (3×50 mL), organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Crude compound was purified by column chromatography using 100-200 mesh silica gel. The column was eluted with 40% EtOAc in petroleum ether to afford the title compound as a yellow solid.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (3×50 mL), organic layer
  3. washwas washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customCrude compound was purified by column chromatography
  7. washThe column was eluted with 40% EtOAc in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-c792ba2d334042f8bf03c49549f5aa95
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321748B2

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