Benzaldehyde, 4-(phenylmethoxy)- → Ethyl 2-(4-benzyloxy-phenyl)-5-(4-fluorophenyl)imidazole-4-carboxylate

HRID 1595429Notes

Reaction equation

HRID 1595429 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9](=[N:15]O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH2:18]([O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])(=O)C.[NH4+:38]>>[CH2:18]([O:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]2[NH:38][C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:15]=2)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 517165Ammonium AcetateHCID 178472897HCID 178472897, compound

Product 1

HCID 178470217Ethyl 2-(4-benzyloxy-phenyl)-5-(4-fluorophenyl)imidazole-4-carboxylate

Procedure

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

Workup

  1. additiontreated in the same manner as in Example 22

Sources & evidence

ORD record
ord-75d0edab26e34e4f9534a056e7aa304e
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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