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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Pyrazine-2-Carboxylic Acid Hydrazide → 7-[(2,4-Dichlorophenyl)carbonyl]-3-(2-pyrazinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1889078
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HRID 1889078 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=O)[CH2:12]1)=[O:10].F[B-](F)(F)F.C([O+](CC)CC)C.[N:30]1[CH:35]=[CH:34][N:33]=[CH:32][C:31]=1[C:36]([NH:38][NH2:39])=O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][N:14]2[C:36]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][N:30]=3)=[N:38][N:39]=[C:13]2[CH2:12]1)=[O:10]
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참가 물질

5

반응물 3

HCID 258796Pyrazine-2-Carboxylic Acid HydrazideHCID 2723982Triethyloxonium tetrafluoroborateHCID 302889354-(2,4-Dichlorobenzoyl)piperazin-2-one

생성물 1

HCID 665988177-[(2,4-Dichlorophenyl)carbonyl]-3-(2-pyrazinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 4-[(2,4-dichlorophenyl)carbonyl]-2-piperazinone (I6) (0.273 g, 1 mmol) in dry Dichloromethane (DCM) (3 ml) was stirred at room temperature under argon. Triethyloxonium tetrafluoroborate (0.199 g, 1.050 mmol) was added and the reaction solution was stirred for 10 minutes. 2-pyrazinecarbohydrazide (0.166 g, 1.200 mmol, commercially available) was then added and the solution was stirred for a further 1 hour. The solvent was then concentrated before n-butanol (3.00 ml) was added and the solution was stirred, under reflux and argon, for 4 hours. LCMS confirmed product location, thus the solution was cooled to room temperature before the solvent was evaporated in vacuo. The remaining residue was then purified by flash chromatograpghy (Biotage SP4, 25M cartridge) with a gradient of 0 to 10% 2M NH3/MeOH in DCM. TLC confirmed product location and the solvent from the combined fractions was evaporated in vacuo. The remaining residue was then further purified by mass-directed automated HPLC. The solvent was then evaporated in vacuo, and the remaining solid was triturated with ether, and dried in a vacuum oven to yield the product in 0.137 g.

후처리

  1. stirringthe solution was stirred for a further 1 hour
  2. concentrationThe solvent was then concentrated before n-butanol (3.00 ml)
  3. additionwas added
  4. stirringthe solution was stirred
  5. temperatureunder reflux
  6. waitargon, for 4 hours
  7. customwas evaporated in vacuo
  8. customThe remaining residue was then purified by flash chromatograpghy (Biotage SP4, 25M cartridge) with a gradient of 0 to 10% 2M NH3/MeOH in DCM
  9. customthe solvent from the combined fractions was evaporated in vacuo
  10. customThe remaining residue was then further purified
  11. customThe solvent was then evaporated in vacuo
  12. customthe remaining solid was triturated with ether
  13. customdried in a vacuum oven
  14. customto yield the product in 0.137 g

출처 및 근거

ORD 기록
ord-25c4e5021d5a4953916ab1a7ec753df5
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501946B2

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