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

HRID 729618노트

반응식

HRID 729618 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-57a70230a3bf4ae287e5f288719c0262
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582638B2

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