Phosphorus oxychloride → HCID 178463643, compound

HRID 1110847Notes

Reaction equation

HRID 1110847 reaction equation
[NH2:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]#[N:8].[CH2:9]([N:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:17](=O)[CH3:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[C:20]1([N:16]([C:17](=[N:1][C:2]2[NH:6][CH:5]=[N:4][C:3]=2[C:7]#[N:8])[CH3:18])[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 3760923N-benzyl-N-phenylacetamideHCID 178510601HCID 178510601, compound

Product 1

HCID 178463643HCID 178463643, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Aminoimidazole-4-carbonitrile is condensed with N-benzyl-N-phenyl-acetamide in the presence of phosphoryl chloride in acetonitrile at room temperature to yield 5-[1-(N-phenyl-N-benzylamino)ethylideneamino]-imidazole-4-carbonitrile. Such is cyclized with sodium hydride in dioxane to yield 7-amino-N-phenyl-N-benzyl-3H-imidazo[4,5-b]pyridine-5-amine. Hydrogenolysis in ethanol with palladium on charcoal yields 7-amino-N-phenyl-3H-imidazo[4,5-b]pyridine-5-amine.

Sources & evidence

ORD record
ord-e23d4ca7fc574d468e83dde148fd7074
Source dataset
uspto-grants-1990_12
Patent number
US04977144

Reaction notes

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