Benzaldehyde → N-{2-[(2-hydroxy-3-methyl-4-oxo-3-phenyl-cyclobut-1-enyl)-phenyl-methyl]-6-methyl-1H-indol-3-ylmethyl}-acetamide

HRID 646066Notes

Reaction equation

HRID 646066 reaction equation
[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5](=[O:6])[CH2:4][C:3]1=[O:7].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:22][C:23]1[CH:31]=[C:30]2[C:26]([C:27]([CH2:32][NH:33][C:34](=[O:36])[CH3:35])=[CH:28][NH:29]2)=[CH:25][CH:24]=1>>[OH:6][C:5]1[C:2]([CH3:1])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3](=[O:7])[C:4]=1[CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:28]1[NH:29][C:30]2[C:26]([C:27]=1[CH2:32][NH:33][C:34](=[O:36])[CH3:35])=[CH:25][CH:24]=[C:23]([CH3:22])[CH:31]=2

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 68580773N-(6-Methyl-1H-indol-3-ylmethyl)-acetamideHCID 685810272-Methyl-2-phenyl-cyclobutane-1,3-dione

Product 1

HCID 25050704N-{2-[(2-hydroxy-3-methyl-4-oxo-3-phenyl-cyclobut-1-enyl)-phenyl-methyl]-6-methyl-1H-indol-3-ylmethyl}-acetamide

Procedure

Using general procedure C, 2-methyl-2-phenyl-cyclobutane-1,3-dione (Lit. 1) was reacted with benzaldehyde and N-(6-methyl-1H-indol-3-ylmethyl)-acetamide to give N-{2-[(2-hydroxy-3-methyl-4-oxo-3-phenyl-cyclobut-1-enyl)-phenyl-methyl]-6-methyl-1H-indol-3-ylmethyl}-acetamide as a pale red solid. MS: 463.4 ([M−H]−).

Sources & evidence

ORD record
ord-777026438ad744278570d99af1002a29
Source dataset
uspto-grants-2010_04
Patent number
US07705034B2

Reaction notes

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