Potassium Carbonate → (2-Fluoro-phenyl)-[4-(4-nitro-isoquinolin-1-yl)-piperazin-1-yl]-methanone

HRID 729617노트

반응식

HRID 729617 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:9].C([O-])([O-])=O.[K+].[K+].Cl[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([N+:33]([O-:35])=[O:34])=[CH:25][N:24]=1>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([N:10]1[CH2:11][CH2:12][N:13]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([N+:33]([O-:35])=[O:34])=[CH:25][N:24]=2)[CH2:14][CH2:15]1)=[O:9]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 544862(2-Fluoro-phenyl)-piperazin-1-yl-methanoneHCID 227654811-Chloro-4-nitroisoquinoline

생성물 1

HCID 69055062(2-Fluoro-phenyl)-[4-(4-nitro-isoquinolin-1-yl)-piperazin-1-yl]-methanone수율 75.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Add (2-fluoro-phenyl)-piperazin-1-yl-methanone (3.16 g, 12.9 mmol) and K2CO3 (8.9 g, 64.5 mmol) to 1-chloro-4-nitroisoquinoline (2.85 g, 13.7 mmol) in acetonitrile (100 mL) and stir for 24 hours. Filter the insoluble solid and wash the cake with AcOEt. Evaporate the solvent under reduced pressure to give a residue. Subject residue to silica gel chromatography eluting with hexane:AcOEt 20-90% to give 3.72 g of (2-fluoro-phenyl)-[4-(4-nitro-isoquinolin-1-yl)-piperazin-1-yl]-methanone as a solid. LCMS ES+(m/z) 381.2 [M+H].

후처리

  1. filtrationFilter the insoluble solid
  2. washwash the cake with AcOEt
  3. customEvaporate the solvent under reduced pressure
  4. customto give a residue
  5. washSubject residue to silica gel chromatography eluting with hexane

출처 및 근거

ORD 기록
ord-26eeef3bb3aa40daadd9e681add3e188
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582638B2

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