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

HRID 1045708노트

반응식

HRID 1045708 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-715da270ac714dcf8602adffb617e3c7
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569300B2

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