HCID 58378151, compound → HCID 58378166, compound

HRID 548613Notes

Reaction equation

HRID 548613 reaction equation
COC1C=CC(C[N:8]2[CH2:13][CH2:12][N:11]3[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:23]([F:26])([F:25])[F:24])=[N:15][CH:16]=[C:10]3[CH2:9]2)=CC=1>CO.[OH-].[OH-].[Pd+2]>[F:26][C:23]([F:24])([F:25])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]1[N:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]2=[CH:16][N:15]=1

Participants

4

Reactant 1

HCID 58378151HCID 58378151, compound

Product 1

HCID 58378166HCID 58378166, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-(4-methoxybenzyl)-3-(2-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine (Step F, 25 mg) in methanol, at 0° C. and under a nitrogen atmosphere was added palladium hydroxide on carbon (15 mg, 20 wt % Pd-Degussa type, E101) and the contents hydrogenated at 40 psi for 14 hours. The reaction mixture was filtered and the filter cake washed with methanol (2×10 mL). The filtrate was concentrated under reduced pressure and azeotroped with dichloromethane (2×20 mL) and ethyl acetate (2×20 mL). The oil that is obtained g (20 mgs) was used as such for the subsequent step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake washed with methanol (2×10 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customazeotroped with dichloromethane (2×20 mL) and ethyl acetate (2×20 mL)
  5. customThe oil that is obtained
  6. customwithout further purification

Sources & evidence

ORD record
ord-e92ca44e51ef43008830cbd88a5a661a
Source dataset
uspto-grants-2011_05
Patent number
US07943617B2

Reaction notes

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