2-Furanacetonitrile, alpha-amino- → alpha-(Imidazo[1,2-a]pyridin-5-ylcarbonylamino)-(2-furyl)acetonitrile
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]=12Participants
4
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.