4-(3-Dimethylaminoazetidin-1-yl)piperidine-1-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide → 4-(3-Dimethylaminoazetidin-1-yl)piperidine-1-carboxylic acid [4-(4-amino-2-fluorophenoxy)pyridin-2-yl]amide

HRID 492966Notes

Reaction equation

HRID 492966 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:23][CH:22]([N:24]([CH3:26])[CH3:25])[CH2:21]3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1>O1CCCC1.[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[CH2:21][CH:22]([N:24]([CH3:25])[CH3:26])[CH2:23]4)[CH2:16][CH2:15]3)=[O:13])[CH:6]=2)=[C:2]([F:1])[CH:30]=1

Participants

4

Reactant 1

HCID 576776984-(3-Dimethylaminoazetidin-1-yl)piperidine-1-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide

Product 1

HCID 576776534-(3-Dimethylaminoazetidin-1-yl)piperidine-1-carboxylic acid [4-(4-amino-2-fluorophenoxy)pyridin-2-yl]amideYield 97.9%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-dimethylaminoazetidin-1-yl)piperidine-1-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide (258 mg) in tetrahydrofuran (50 ml) was added 20% palladium hydroxide carbon (198 mg), followed by stirring under a hydrogen atmosphere at room temperature for 12 hrs. The reaction mixture was filtered to remove the catalyst, and the catalyst was washed with tetrahydrofuran:methanol=1:1. The filtrate was concentrated to provide the titled compound (236 mg, 97.8%) as a yellow amorphous substance.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. washthe catalyst was washed with tetrahydrofuran
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fc318a0106884e84bc4ab173172c9583
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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