HCID 57677470, compound → 4-(4-Aminophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridine

HRID 2066261Notes

Reaction equation

HRID 2066261 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 57677470HCID 57677470, compound

Product 1

HCID 231532634-(4-Aminophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridineYield 105.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Pyrrolidine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide (116.8 mg) was dissolved in tetrahydrofuran (3 ml), 20% palladium hydroxide on carbon (25.0 mg) was added under a nitrogen atmosphere at room temperature while stirring, followed by stirring under a hydrogen atmosphere for 7 hr. The atmosphere in the reaction vessel was replaced with nitrogen, and the catalyst was removed by filtration and washed with tetrahydrofuran. The solvent was removed under reduced pressure to provide the titled compound as a pale yellow solid (112 mg).

Workup

  1. stirringby stirring under a hydrogen atmosphere for 7 hr
  2. customthe catalyst was removed by filtration
  3. washwashed with tetrahydrofuran
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f6f2ca489f7348499ff63476397f2cba
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

Loading…