N-[4-(4-nitrophenoxy)-2-pyridinyl]-4-morpholinecarboxamide → HCID 57677741, compound

HRID 2066259Notes

Reaction equation

HRID 2066259 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][O: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:25]=[CH:24][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 57677759N-[4-(4-nitrophenoxy)-2-pyridinyl]-4-morpholinecarboxamide

Product 1

HCID 57677741HCID 57677741, compoundYield 103.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Morpholine-4-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide (128 mg) was dissolved in tetrahydrofuran (3 ml), and 20% palladium hydroxide on carbon (26.3 mg) was added at room temperature under a nitrogen atmosphere, 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 (121 mg).

Workup

  1. customthe catalyst was removed by filtration
  2. washwashed with tetrahydrofuran
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-45b98987e44245fba326cfe4433075d7
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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