8-Chloro-3-(2,4-difluorophenyl)imidazo[1,5-a]pyrazine → 3-(2,4-Difluorophenyl)-5,6,7,8-tetrahydroimidazo[1,5-A]pyrazine

HRID 548615Notes

Reaction equation

HRID 548615 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=3[F:18])=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1>CO.[Pd]>[F:18][C:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[C:8]1[N:4]2[CH2:5][CH2:6][NH:7][CH2:2][C:3]2=[CH:10][N:9]=1

Participants

4

Reactant 1

HCID 583781348-Chloro-3-(2,4-difluorophenyl)imidazo[1,5-a]pyrazine

Product 1

HCID 341763183-(2,4-Difluorophenyl)-5,6,7,8-tetrahydroimidazo[1,5-A]pyrazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-chloro-3-(2,4-difluorophenyl)imidazo[1,5-a]pyrazine (Step C, 200 mg) in methanol, at 0° C. and under a nitrogen atmosphere was added palladium on carbon (75 mgs, 10 wt % Pd) and the contents hydrogenated at 50 psi for 20 hours. The reaction mixture was filtered and the filter cake washed with methanol (2×10 mL). The filtrate was concentrated under reduced pressure to yield a solid d (175 mgs) that 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. customto yield a solid d (175 mgs) that
  5. customwithout further purification

Sources & evidence

ORD record
ord-5ca0222bf06a4a9a9668c92459f6d1bb
Source dataset
uspto-grants-2011_05
Patent number
US07943617B2

Reaction notes

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