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

HRID 646072Notes

Reaction equation

HRID 646072 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.[Cl:23][C:24]1[CH:32]=[C:31]2[C:27]([C:28]([CH2:33][NH:34][C:35](=[O:37])[CH3:36])=[CH:29][NH:30]2)=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:32]=[C:31]2[C:27]([C:28]([CH2:33][NH:34][C:35](=[O:37])[CH3:36])=[C:29]([CH:15]([C:4]3[C:3](=[O:7])[C:2]([CH3:1])([C:8]4[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=4)[C:5]=3[OH:6])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:30]2)=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 68579881N-(6-chloro-1H-indol-3-ylmethyl)-acetamideHCID 685819552-Methyl-2-p-tolyl-cyclobutane-1,3-dione

Product 1

HCID 59264909N-{6-Chloro-2-[(2-hydroxy-3-methyl-4-oxo-3-p-tolyl-cyclobut-1-enyl)-phenyl-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-(6-chloro-1H-indol-3-ylmethyl)-acetamide (prepared from C-(6-chloro-1H-indol-3-yl)-methylamine by acylation according to Example 1.2) to give the title compound as an off-white solid. MS: 497.3 ([M−H]−).

Sources & evidence

ORD record
ord-b559751b456747f1b7b7b2f150a7eeec
Source dataset
uspto-grants-2010_04
Patent number
US07705034B2

Reaction notes

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