N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide → 1-(5-amino-pyrazin-2-yl)-ethanone O-tert-butyl-oxime

HRID 719892ノート

反応式

HRID 719892 の反応式
[C:1]([O:5][N:6]=[C:7]([C:9]1[N:10]=[CH:11][C:12]([NH:15]C(=O)C(C)(C)C)=[N:13][CH:14]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.O.NN.C(OCC)(=O)C>[C:1]([O:5][N:6]=[C:7]([C:9]1[CH:14]=[N:13][C:12]([NH2:15])=[CH:11][N:10]=1)[CH3:8])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 1

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

生成物 1

HCID 865937831-(5-amino-pyrazin-2-yl)-ethanone O-tert-butyl-oxime収率 101,606.602%

試薬・触媒・溶媒 3

HCID 8857Ethyl Acetate溶媒HCID 24654Hydrazine hydrate (1:1)溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
25 °C

実験手順

A solution of N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide (563.4 mg, 1.93 mmol) in dioxane (5.8 mL) and hydrazine monohydrate (9.6 mL) was heated under reflux for 48 h. The reaction mixture was allowed to cool to 25° C. and then was diluted with ethyl acetate (100 mL). The organic layer was washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 3/7 ethyl acetate/hexanes) afforded 1-(5-amino-pyrazin-2-yl)-ethanone O-tert-butyl-oxime (408.4 g, quant.) as a light yellow solid: mp 113–115° C.; EI-HRMS m/e calcd for C10H16N4O (M+) 208.1324, found 208.1325.

後処理

  1. temperatureunder reflux for 48 h
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution (1×100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-698414e486ed4cc899c2fa1774c1054e
出典データセット
uspto-grants-2006_11
特許番号
US07132425B2

反応ノート

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