Benzaldehyde, 4-(phenylmethoxy)- → Ethyl 2-(4-benzyloxyphenyl)-5-(4-methoxyphenyl)imidazole-4-carboxylate

HRID 1595425Notes

Reaction equation

HRID 1595425 reaction equation
O[N:2]=[C:3]([C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:19]([O:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])(=O)C.[NH4+:39]>>[CH2:19]([O:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]2[NH:39][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:2]=2)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 517165Ammonium AcetateHCID 178472900HCID 178472900, compound

Product 1

HCID 178470218Ethyl 2-(4-benzyloxyphenyl)-5-(4-methoxyphenyl)imidazole-4-carboxylate

Procedure

Ethyl 2-hydroxyimino-3-(4-methoxyphenyl)-3-oxopropionate, 4-benzyloxybenzaldehyde and ammonium acetate are reacted and treated in the same manner as in Example 22 to give ethyl 2-(4-benzyloxyphenyl)-5-(4-methoxyphenyl)imidazole-4-carboxylate. Ethyl 2-(4-benzyloxyphenyl)-5-(4-methoxyphenyl)imidazole-4-carboxylate is reacted and treated in the same manner as in Starting Material Synthetic Example 2 to give 2-(4-benzyloxyphenyl)-5-(4-methoxyphenyl)imidazole-4-carboxylic acid. 2-(4-Benzyloxyphenyl)-5-(4-methoxyphenyl)imidazole-4-carboxylic acid is reacted and treated in the same manner as in Example 1 to give 2-(4-benzyloxyphenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide.

Workup

  1. additiontreated in the same manner as in Example 22

Sources & evidence

ORD record
ord-5fa9e350dc75478185a397b411e8330d
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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