Hydrazine hydrate (1:1) → Tert-butyl 4-(5-bromo-3-hydrazinylpyrazin-2-yl)piperazine-1-carboxylate

HRID 1045708ノート

反応式

HRID 1045708 の反応式
[Br:1][C:2]1[N:3]=[C:4](Cl)[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.O.[NH2:23][NH2:24]>C(O)C>[Br:1][C:2]1[N:3]=[C:4]([NH:23][NH2:24])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 58447006Tert-butyl 4-(5-bromo-3-chloropyrazin-2-yl)piperazine-1-carboxylate

生成物 1

HCID 58447020Tert-butyl 4-(5-bromo-3-hydrazinylpyrazin-2-yl)piperazine-1-carboxylate収率 47%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A 500 mL 3-necked round bottom flask was charged with tert-butyl 4-(5-bromo-3-chloropyrazin-2-yl)piperazine-1-carboxylate (16.1 g, 42.6 mmol), hydrazine hydrate (4.2 mL, 85.2 mmol) and ethanol (200 mL). The resulting solution was refluxed overnight. TLC indicated an incomplete conversion. The solvent was evaporated and the residue was purified by flash column chromatography on silica gel with 10% EtOAc in petroleum ether then 2% methanol in dichloromethane, to afford 5.8 g (47%) of the product as a yellow solid. MS m/z: 373 (M+H+).

後処理

  1. temperatureThe resulting solution was refluxed overnight
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash column chromatography on silica gel with 10% EtOAc in petroleum ether

出典と根拠

ORDレコード
ord-715da270ac714dcf8602adffb617e3c7
出典データセット
uspto-grants-2013_10
特許番号
US08569300B2

反応ノート

読み込み中…