2-{[4-(Dimethylaminomethyl)piperidin-1-yl]carbonylamino}-4-(2-fluoro-4-nitrophenoxy)pyridine → HCID 23153096, compound

HRID 2066183Notes

Reaction equation

HRID 2066183 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][C:22]=3[F:30])[CH:17]=[CH:16][N:15]=2)=[O:12])[CH2:7][CH2:6]1)[CH3:3]>O1CCCC1.[OH-].[OH-].[Pd+2]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:18]2[CH:17]=[CH:16][N:15]=[C:14]([NH:13][C:11]([N:8]3[CH2:7][CH2:6][CH:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH2:10][CH2:9]3)=[O:12])[CH:19]=2)=[C:22]([F:30])[CH:23]=1

Participants

4

Reactant 1

HCID 231536182-{[4-(Dimethylaminomethyl)piperidin-1-yl]carbonylamino}-4-(2-fluoro-4-nitrophenoxy)pyridine

Product 1

HCID 23153096HCID 23153096, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-{[4-(Dimethylaminomethyl)piperidin-1-yl]carbonylamino}-4-(2-fluoro-4-nitrophenoxy)pyridine (183 mg) was dissolved in tetrahydrofuran (20 ml). 20% palladium hydroxide on carbon (123 mg) was added thereto, followed by stirring under a hydrogen atmosphere overnight. The catalyst was removed by filtration and washed with tetrahydrofuran. The filtrate and the washing were combined and concentrated under reduced pressure, the resultant residue was dried under reduced pressure to provide the titled compound as pale yellow powder (167 mg, 98%).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with tetrahydrofuran
  3. concentrationconcentrated under reduced pressure
  4. dry with materialthe resultant residue was dried under reduced pressure

Sources & evidence

ORD record
ord-b2ae1741742c4c03bab4b5afe38c4cbe
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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