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

HRID 719891노트

반응식

HRID 719891 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 73852558N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide수율 98.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1049Pyridine용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6d561c83aa3046cf96d68aef89b367f8
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132425B2

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