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

HRID 1158847Notes

Reaction equation

HRID 1158847 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-41e3660689e54c86990956921ccca778
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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