1,4-Cyclohexadiene → HCID 178461466, compound

HRID 1696226Notes

Reaction equation

HRID 1696226 reaction equation
[ClH:1].Cl.C([N:10]1[CH2:15][CH2:14][C@@H:13]([CH3:16])[C@@H:12]([N:17]([CH3:27])[C:18]2[CH:23]=[CH:22][N:21]=[C:20]3[NH:24][CH:25]=[N:26][C:19]=23)[CH2:11]1)C1C=CC=CC=1.C1CC=CCC=1>C(O)C.[OH-].[OH-].[Pd+2]>[ClH:1].[ClH:1].[CH3:27][N:17]([C@@H:12]1[C@H:13]([CH3:16])[CH2:14][CH2:15][NH:10][CH2:11]1)[C:18]1[CH:23]=[CH:22][N:21]=[C:20]2[NH:24][CH:25]=[N:26][C:19]=12

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 178461465HCID 178461465, compound

Product 1

HCID 178461466HCID 178461466, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

In a microwave reaction vessel, to a solution of rel-N-[(3R,4R)-1-benzyl-4-methyl-3-piperidinyl]-N-methyl-3H-imidazo[4,5-b]pyridin-7-amine dihydrochloride (130 mg) in ethanol (1.3 mL) were added 1,4-cyclohexadiene (1.5 mL) and palladium hydroxide on carbon (130 mg). The vessel was sealed and reacted in the microwave reactor at 110° C. for 0.5 hour. The reaction mixture was cooled to ambient temperature and filtrated through a pad of Celite. The filtrate was concentrated under reduced pressure and the residue was washed with diisopropyl ether to give N-methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]-3H-imidazo[4,5-b]pyridin-7-aminedihydrochloride (48 mg) as a white powder.

Workup

  1. customIn a microwave reaction vessel
  2. customThe vessel was sealed
  3. customreacted in the microwave reactor at 110° C. for 0.5 hour
  4. filtrationfiltrated through a pad of Celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-9c5dfae712514989900f6b61885e0e96
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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