Triethylamine → 3-Cyano-methyl-2-methyl-8-(2-phenylethyl)imidazo[1,2-a]pyridine

HRID 544454Notes

Reaction equation

HRID 544454 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH:17]([C:21](=O)C)[CH2:18][C:19]#[N:20].[CH2:24](N(CC)CC)C>C(O)C>[C:19]([C:18]1[N:3]2[C:4]([CH3:24])=[CH:5][CH:6]=[C:7]([CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:2]2=[N:1][C:17]=1[CH3:21])#[N:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 139002352-Amino-3-(2-phenylethyl)pyridineHCID 139002363-Chloro-4-oxopentanenitrile

Product 1

HCID 705059793-Cyano-methyl-2-methyl-8-(2-phenylethyl)imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In similar manner, reaction of 2-amino-3-(2-phenylethyl)pyridine (which is prepared by amination of 3-(2-phenyl ethyl)-pyridine with sodium amide in ammonia and N,N-dimethylaniline) with 3-chloro-4-oxo-pentanonitrile in ethanol in the presence of triethylamine gives 3-cyano-methyl-2-methyl-8-(2-phenylethyl)imidazo[1,2-a]pyridine.

Sources & evidence

ORD record
ord-382b7b5ab5964d11afc889f3a014c562
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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