HCID 59374159, compound → HCID 59373929, compound

HRID 473645Notes

Reaction equation

HRID 473645 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][N:22]=4)=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH3:27][C:26]1[C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][C:8]3[C:7]([CH:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[CH:12][CH:11]=[CH:10][N:9]=3)=[CH:15][CH:16]=2)=[N:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 59374159HCID 59374159, compound

Product 1

HCID 59373929HCID 59373929, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a pressure vessel was added N-(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)-3-methylpyridin-2-amine (0.2400 g, 0.668 mmol) and palladium hydroxide on carbon (0.047 g, 0.067 mmol) in EtOAc (2.226 mL). The rbf was flushed with nitrogen and then placed under vacuum three times. Reaction was placed under 40 psi. Reaction mixture was filtered through celite. The crude product was adsorbed onto a plug of silica gel and chromatographed to provide 3-methyl-N-(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)pyridin-2-amine. MS (ESI, pos. ion) m/z: 362.1. IC50 (uM) 0.006873.

Workup

  1. customThe rbf was flushed with nitrogen
  2. customReaction
  3. customReaction mixture
  4. filtrationwas filtered through celite
  5. customchromatographed

Sources & evidence

ORD record
ord-8c071c5f794b4b919ccc04b6aa4d07a9
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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