1-(1H-Imidazol-1-yl)ethanone → HCID 22724269, compound

HRID 2086891Notes

Reaction equation

HRID 2086891 reaction equation
Br[CH2:2][C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N:16]3[C:20](=[O:21])[CH2:19][CH2:18][C:17]3=[O:22])[CH:11]=2)[C:6]2[N:23]=[CH:24][CH:25]=[CH:26][C:5]=2[N:4]=1.C([N:30]1[CH:34]=[CH:33][N:32]=[CH:31]1)(=O)C>C(#N)C>[NH:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH2:2][C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N:16]3[C:20](=[O:21])[CH2:19][CH2:18][C:17]3=[O:22])[CH:11]=2)[C:6]2[N:23]=[CH:24][CH:25]=[CH:26][C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 22724279HCID 22724279, compound

Product 1

HCID 22724269HCID 22724269, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(bromomethyl)-4-(3-succinimidophenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (420 mg) in acetonitrile (4 ml) was added 1-acetylimidazole (179 mg). The solution was refluxed for an hour. The mixture was evaporated. The residue was dissolved in water, and to the solution was added sodium carbonate. The mixture was extracted by ethyl acetate. The organic layer was evaporated. The residue was purified by column chromatography to obtain 2-(1-imidazolylmethyl)-4-(3-succinimidophenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (105 mg) as yellow powder.

Workup

  1. temperatureThe solution was refluxed for an hour
  2. customThe mixture was evaporated
  3. dissolutionThe residue was dissolved in water
  4. additionto the solution was added sodium carbonate
  5. extractionThe mixture was extracted by ethyl acetate
  6. customThe organic layer was evaporated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-35508f66790e4970aa673f823c9b0de3
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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