N-[4-[[3-(3,4-Dihydro-2H-pyran-2-yl)-2-pyridinyl]oxy]phenyl]-2-pyridinamine → N-[4-[[3-(Tetrahydro-2H-pyran-2-yl)-2-pyridinyl]oxy]phenyl]-2-pyridinamine

HRID 473660Notes

Reaction equation

HRID 473660 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH:2]1[C:7]1[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:16][CH:15]=2)=[N:9][CH:10]=[CH:11][CH:12]=1>[Pd].CCO.O1CCOCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]1[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:16][CH:15]=2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 59374292N-[4-[[3-(3,4-Dihydro-2H-pyran-2-yl)-2-pyridinyl]oxy]phenyl]-2-pyridinamine

Product 1

HCID 59374005N-[4-[[3-(Tetrahydro-2H-pyran-2-yl)-2-pyridinyl]oxy]phenyl]-2-pyridinamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22560076Dioxan ethanolSolvent

Procedure

A mixture of (±)-N-(4-(3-(3,4-dihydro-2H-pyran-2-yl)pyridin-2-yloxy)phenyl)pyridin-2-amine (233 mg, 0.675 mmol) and palladium on carbon (wet) (71.8 mg, 0.067 mmol) in EtOH/dioxane was placed under an atmosphere of hydrogen gas and stirred for 24 hours. The mixture was then filtered through a cake of celite, washing with MeOH. The filtrate was concentrated and purified by silica gel chromatography, 10-100% acetone/hexanes, to give the title compound as a racemic mixture. MS (ESI, pos. ion) m/z: 348.0 (M+1). IC50 (uM) 0.149.

Workup

  1. filtrationThe mixture was then filtered through a cake of celite
  2. washwashing with MeOH
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel chromatography, 10-100% acetone/hexanes

Sources & evidence

ORD record
ord-5d2b6b705da94798908a58bc1a02b849
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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