HCID 59374240, compound → HCID 59373972, compound

HRID 473675Notes

Reaction equation

HRID 473675 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]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=4)=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[F: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)=[N: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 59374240HCID 59374240, compound

Product 1

HCID 59373972HCID 59373972, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a round-bottomed flask was added N-(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)phenyl)-3-fluoropyridin-2-amine (0.1433 g, 0.393 mmol) in ethyl acetate. Palladium hydroxide (0.028 g, 0.039 mmol) was added. The rxn was placed under 40 psi pressure. The reaction mixture was filtered through celite. The crude product was adsorbed onto a plug of silica gel and chromatographed to provide 3-fluoro-N-(4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine. MS (ESI, pos. ion) m/z: 367.1 (M+1). IC50 (uM) 0.01772.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customchromatographed

Sources & evidence

ORD record
ord-4acdba608258451385fe20ac8ef9ab22
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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