O-tert-butylhydroxylamine hydrochloride → N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide

HRID 719891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 719891
[C:1]([C:4]1[N:5]=[CH:6][C:7]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:8][CH:9]=1)(=O)[CH3:2].Cl.[C:18]([O:22][NH2:23])([CH3:21])([CH3:20])[CH3:19]>CO.N1C=CC=CC=1>[C:18]([O:22][N:23]=[C:1]([C:4]1[N:5]=[CH:6][C:7]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:8][CH:9]=1)[CH3:2])([CH3:21])([CH3:20])[CH3:19]

Komponenten

5

Edukt 2

HCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 21897264N-(5-acetylpyrazin-2-yl)-2,2-dimethylpropanamide

Produkt 1

HCID 73852558N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamideAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of N-(5-acetyl-pyrazin-2-yl)-2,2-dimethyl-propionamide (800.0 mg, 3.62 mmol) in methanol (9 mL) and pyridine (9 mL) was treated with O-(tert-butyl)hydroxylamine hydrochloride (681.1 mg, 5.42 mmol). The resulting reaction mixture was heated under reflux for 30 min. The reaction mixture was allowed to cool to 25° C. and then was concentrated in vacuo. The resulting residue was diluted with ethyl acetate (50 mL). The organic layer was washed with a 1N aqueous hydrochloric acid solution (1×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 1/9 ethyl acetate/hexanes) afforded N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide (1.04 g, 98%) as a white solid: mp 123–124° C.; EI-HRMS m/e calcd for C15H24N4O2 (M+) 292.1899, found 292.1901.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 30 min
  4. concentrationwas concentrated in vacuo
  5. additionThe resulting residue was diluted with ethyl acetate (50 mL)
  6. washThe organic layer was washed with a 1N aqueous hydrochloric acid solution (1×50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6d561c83aa3046cf96d68aef89b367f8
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132425B2

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