2-Furanacetonitrile, alpha-amino- → alpha-(Imidazo[1,2-a]pyridin-5-ylcarbonylamino)-(2-furyl)acetonitrile

HRID 1440474Notes

Reaction equation

HRID 1440474 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([NH2:9])[C:7]#[N:8].[N:10]1[CH:11]=[CH:12][N:13]2[C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=12>C(#N)C>[N:10]1[CH:11]=[CH:12][N:13]2[C:18]([C:19]([NH:9][CH:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[C:7]#[N:8])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=12

Participants

4

Reactant 2

HCID 111477062-Furanacetonitrile, alpha-amino-HCID 54354734Imidazo[1,2-a]pyridine-5-carboxylic acid chloride

Product 1

HCID 18983877alpha-(Imidazo[1,2-a]pyridin-5-ylcarbonylamino)-(2-furyl)acetonitrileYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

α-(2-Furyl)-α-aminoacetonitrile (0.7 g, 5.5 m moles) was dissolved in acetonitrile (20 ml), and imidazo[1,2-a]pyridine-5-carboxylic acid chloride (1.0 g, 5.5 m moles) was added thereto and reacted at room temperature for 2 hours. After completion of the reaction, the solvent was removed from the reaction mixture. To the residue were added water (20 ml), saturated aqueous solution of sodium bicarbonate (50 ml) and chloroform (50 ml), and the mixture was stirred. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by column chromatography on silica gel (eluent: methanol/chloroform=1/9) to give the object compound (0.9 g, yield 64%) as amorphous solid.

Workup

  1. customreacted at room temperature for 2 hours
  2. customAfter completion of the reaction
  3. customthe solvent was removed from the reaction mixture
  4. additionTo the residue were added water (20 ml), saturated aqueous solution of sodium bicarbonate (50 ml) and chloroform (50 ml)
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by column chromatography on silica gel (eluent: methanol/chloroform=1/9)

Sources & evidence

ORD record
ord-a21315f8e7394331bdcdcccd9ecd41ba
Source dataset
uspto-grants-1996_03
Patent number
US05498774

Reaction notes

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