Water → HCID 66733890, compound

HRID 1929693Notes

Reaction equation

HRID 1929693 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][C:16](I)=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([C:29]([F:32])([F:31])[F:30])=[CH:24][C:23]=1[F:33])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O>[Pd].CO.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][CH:16]=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([C:29]([F:31])([F:32])[F:30])=[CH:24][C:23]=1[F:33])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 66733974HCID 66733974, compound

Product 1

HCID 66733890HCID 66733890, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-[2-(2,5-difluoro-4-trifluoromethyl-phenyl)-ethyl]-3-ethyl-1-iodo-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (1.890 g; 3.229 mmol), 10% palladium on activated charcoal (567 mg), and anhydrous potassium carbonate (1.115 g; 8.072 mmol; 2.5 eq.) in anhydrous MeOH (75 ml) was stirred at rt, under hydrogen (1 atm), for 3 h15. Filtration over a pad of celite, and subsequent concentration to dryness afforded a crude heterogeneous residue which was dissolved in DCM (100 ml), and water (50 ml). The organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure to give 8-[2-(2,5-difluoro-4-trifluoromethyl-phenyl)-ethyl]-3-ethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow oil (1.400 g; 94%). LC-MS: tR=0.94 min.; [M+H]+=460.04 g/mol.

Workup

  1. filtrationFiltration
  2. concentrationover a pad of celite, and subsequent concentration to dryness
  3. customafforded a crude heterogeneous residue which
  4. dry with materialThe organic layer was then dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2870c574198e4d4894e54e263ed3e0bb
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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