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

HRID 729618Notes

Reaction equation

HRID 729618 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-57a70230a3bf4ae287e5f288719c0262
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Reaction notes

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