Tetrahydrofuran → [4-(4-Amino-isoquinolin-1-yl)-piperazin-1-yl]-(2-fluoro-phenyl)-methanone

HRID 729618ノート

反応式

HRID 729618 の反応式
[O-]S(S([O-])=O)=O.[Na+].[Na+].[NH4+].[OH-].[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]([N+:36]([O-])=O)=[CH:28][N:27]=2)[CH2:22][CH2:21]1)=[O:19].C1COCC1>O>[NH2:36][C:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:26]([N:23]2[CH2:24][CH2:25][N:20]([C:18]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[F:11])=[O:19])[CH2:21][CH2:22]2)=[N:27][CH:28]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 69055062(2-Fluoro-phenyl)-[4-(4-nitro-isoquinolin-1-yl)-piperazin-1-yl]-methanone

生成物 1

HCID 57832822[4-(4-Amino-isoquinolin-1-yl)-piperazin-1-yl]-(2-fluoro-phenyl)-methanone収率 65.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

Add Na2S2O4 (60.87 g, 39.4 mmol) followed by NH4OH 32% (15 mL) to (2-fluoro-phenyl)-[4-(4-nitro-isoquinolin-1-yl)-piperazin-1-yl]-methanone (3 g, 7.89 mmol) in 170 mL of 1:1 mixture of THF:H2O and stir for 90 min. Dilute with water and extract with AcOEt several times. Combine organics and wash with saturated aq. sodium chloride, dry over Na2SO4 and evaporate under reduced pressure to give 1.8 g of the title compound as a solid. LCMS ES+ (m/z) 351.2 [M+H].

後処理

  1. extractionextract with AcOEt several times
  2. washCombine organics and wash with saturated aq. sodium chloride
  3. dry with materialdry over Na2SO4
  4. customevaporate under reduced pressure

出典と根拠

ORDレコード
ord-57a70230a3bf4ae287e5f288719c0262
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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