ethyl imidazo[1,2-a]pyrazine-2-carboxylate → HCID 11845779, compound

HRID 2216552Notes

Reaction equation

HRID 2216552 reaction equation
[ClH:1].CCO.[CH2:5]([O:7][C:8]([C:10]1[N:11]=[C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]2[CH:18]=1)=[O:9])[CH3:6]>[Pd].CCO>[ClH:1].[CH2:5]([O:7][C:8]([C:10]1[N:11]=[C:12]2[CH2:17][NH:16][CH2:15][CH2:14][N:13]2[CH:18]=1)=[O:9])[CH3:6]

Participants

5

Reactant 2

HCID 11845418ethyl imidazo[1,2-a]pyrazine-2-carboxylateHCID 21887872Ethanol hydrochloride

Product 1

HCID 11845779HCID 11845779, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.46 M HCl-EtOH (169 mL) and 10% Pd—C (50% wet) (1.37 g) were added to the EtOH (546 mL) solution of imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester (13.7 g). The mixture was hydrogenated under H2 at 40 psi at room temperature for 15 h. The reaction mixture was filtered and Pd—C was washed with EtOH. The filtrate was concentrated under reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with CHCl3-MeOH (9/1˜2/1). The titled compound was obtained as brown crystals Yield: 10.4 g, 63%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washPd—C was washed with EtOH
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washthe column was eluted with CHCl3-MeOH (9/1˜2/1)

Sources & evidence

ORD record
ord-8d77dd93ef5a4edcbf74a4742fb44cc8
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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