HCID 59596988, compound → HCID 59596945, compound

HRID 2066263Notes

Reaction equation

HRID 2066263 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[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:23]=[CH:22][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:21][CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 59596988HCID 59596988, compound

Product 1

HCID 59596945HCID 59596945, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Azetidine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide (118.7 mg) was dissolved in tetrahydrofuran (6 ml), and 20% palladium hydroxide on carbon (26.6 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 (110 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-35fc328a212d4d26871c756fe73ae5b6
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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