Triethylamine → 6-Benzylamino-2-methylimidazo[1,2-a]pyridine-3-acetonitrile

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][N:3]=1.C(N(CC)CC)C.Cl[CH:24]([C:28](=O)[CH3:29])[CH2:25][C:26]#[N:27]>C(#N)C>[CH2:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:24]([CH2:25][C:26]#[N:27])=[C:28]([CH3:29])[N:1]=2)[CH:4]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Procedure

A mixture of 2-amino-5-benzylamino pyridine (4.0 g), triethylamine (2.1 g),3-chloro-4-oxopentanenitrile (2.7 g) and acetonitrile (50 ml) is stirred and heated under reflux for 18 hr. The solvent is removed in vacuo, and the residue is dissolved in chloroform (200 ml). The solution is washed with water (4×100 ml), dried over anhydrous potassium carbonate and the chloroform is removed in vacuo. The residue is chromatographed on silica gel (200 g) using chloroform as the eluant. The product is obtainedand crystallized from acetonitrile.