2-Furanacetonitrile, alpha-amino- → alpha-(Imidazo[1,2-a]pyridin-8-ylcarbonylamino)-(2-furyl)acetonitrile

HRID 1440473Notes

Reaction equation

HRID 1440473 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[CH:18]=[CH:17][CH:16]=[C:15]([C:19](Cl)=[O:20])[C:14]=12>C(#N)C>[N:10]1[CH:11]=[CH:12][N:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([NH:9][CH:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[C:7]#[N:8])=[O:20])[C:14]=12

Participants

4

Reactant 2

HCID 111477062-Furanacetonitrile, alpha-amino-HCID 54030396Imidazo[1,2-a]pyridine-8-carboxylic acid chloride

Product 1

HCID 18983849alpha-(Imidazo[1,2-a]pyridin-8-ylcarbonylamino)-(2-furyl)acetonitrileYield 11%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

α-(2-Furyl)-α-aminoacetonitrile (0.7 g, 5.5 m mols) was dissolved in acetonitrile (20 ml), and imidazo[1,2-a]pyridine-8-carboxylic acid chloride (1.0 g, 5.5 m moles) was added thereto with stirring and reacted at room temperature for 2 hours. After completion of the reaction, the solvent was removed from the reaction mixture under reduced pressure. 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:ethyl acetate/n-hexane=2/1) to give the object compound (0.16 g, yield 11%) as crystals. m.p. 149°-151° C.

Workup

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

Sources & evidence

ORD record
ord-f3f95c72f00748b9a942b66332e3f499
Source dataset
uspto-grants-1996_03
Patent number
US05498774

Reaction notes

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