Benzaldehyde → N-{2-[(2-Hydroxy-3-methyl-4-oxo-3-p-tolyl-cyclobut-1-enyl)-phenyl-methyl]-7-methyl-1H-indol-3-ylmethyl}-acetamide

HRID 646073Notes

Reaction equation

HRID 646073 reaction equation
[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:5](=[O:6])[CH2:4][C:3]1=[O:7].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:32]=1[NH:31][CH:30]=[C:29]2[CH2:33][NH:34][C:35](=[O:37])[CH3:36]>>[OH:7][C:3]1[C:2]([CH3:1])([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:5](=[O:6])[C:4]=1[CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:30]1[NH:31][C:32]2[C:28]([C:29]=1[CH2:33][NH:34][C:35](=[O:37])[CH3:36])=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:23]

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 68579310Acetamide,n-[(7-methyl-1h-indol-3-yl)methyl]-HCID 685819552-Methyl-2-p-tolyl-cyclobutane-1,3-dione

Product 1

HCID 59264917N-{2-[(2-Hydroxy-3-methyl-4-oxo-3-p-tolyl-cyclobut-1-enyl)-phenyl-methyl]-7-methyl-1H-indol-3-ylmethyl}-acetamide

Procedure

Using general procedure C, 2-methyl-2-p-tolyl-cyclobutane-1,3-dione (from Example 4.1) was reacted with benzaldehyde and N-(7-methyl-1H-indol-3-ylmethyl)-acetamide (prepared from 7-methyl-1H-indole-3-carbaldehyde according to Example 10.1-10.3) to give the title compound as an off-white solid. MS: 477.4 ([M−H]−).

Sources & evidence

ORD record
ord-ab7cd74ae06247a6a73b7db5bca93256
Source dataset
uspto-grants-2010_04
Patent number
US07705034B2

Reaction notes

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