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

HRID 729618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729618
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 57832822[4-(4-Amino-isoquinolin-1-yl)-piperazin-1-yl]-(2-fluoro-phenyl)-methanoneAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

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].

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-57a70230a3bf4ae287e5f288719c0262
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582638B2

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