水合肼 → Tert-butyl 4-(5-bromo-3-hydrazinylpyrazin-2-yl)piperazine-1-carboxylate

HRID 1045708笔记

反应方程式

HRID 1045708 反应方程式
[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

参与物

4

反应物 2

HCID 24654水合肼HCID 58447006Tert-butyl 4-(5-bromo-3-chloropyrazin-2-yl)piperazine-1-carboxylate

产物 1

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

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

实验过程

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+).

后处理

  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

来源与证据

ORD记录
ord-715da270ac714dcf8602adffb617e3c7
来源数据集
uspto-grants-2013_10
专利号
US08569300B2

反应笔记

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