1H-imidazole-2-carbaldehyde → N-(2-{2-[(2-Hydroxy-5-oxo-3-phenyl-cydopent-1-enyl)-(1H-imidazol-2-yl)-methyl]-1H-indol-3-yl}-ethyl)-acetamide

HRID 1432484Notes

Reaction equation

HRID 1432484 reaction equation
[OH:1][C:2]1[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][C:4](=[O:13])[CH:3]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[C:15]1[CH:19]=O.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][CH2:31][NH:32][C:33](=[O:35])[CH3:34])=[CH:22]1>>[OH:1][C:2]1[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][C:4](=[O:13])[C:3]=1[CH:19]([C:15]1[NH:14][CH:18]=[CH:17][N:16]=1)[C:22]1[NH:21][C:29]2[C:24]([C:23]=1[CH2:30][CH2:31][NH:32][C:33](=[O:35])[CH3:34])=[CH:25][CH:26]=[CH:27][CH:28]=2

Participants

4

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 70547N-AcetyltryptamineHCID 690696643-Hydroxy-4-phenyl-cyclopent-2-enone

Product 1

HCID 57933442N-(2-{2-[(2-Hydroxy-5-oxo-3-phenyl-cydopent-1-enyl)-(1H-imidazol-2-yl)-methyl]-1H-indol-3-yl}-ethyl)-acetamide

Procedure

Using general procedure C, 3-hydroxy-4-phenyl-cyclopent-2-enone (Lit. 17) was reacted with 1H-imidazole-2-carbaldehyde and N-[2-(1H-indol-3-yl)-ethyl]-acetamide to give the title compound as pale brown solid. MS: 455.0 ([M+H]+).

Sources & evidence

ORD record
ord-b8c05baa57e543deb60d8c84a1ed4d75
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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