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

HRID 729617ノート

反応式

HRID 729617 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-26eeef3bb3aa40daadd9e681add3e188
出典データセット
uspto-grants-2009_09
特許番号
US07582638B2

反応ノート

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