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

HRID 646055Notes

Reaction equation

HRID 646055 reaction equation
[CH2:1]([C:8]1([CH3:14])[C:11](=[O:12])[CH2:10][C:9]1=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:23][C:24]([NH:37][C:38](=[O:40])[CH3:39])([CH3:36])[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][C:31]([CH3:35])=[CH:32][CH:33]=2)[NH:28][CH:27]=1>>[CH2:1]([C:8]1([CH3:14])[C:9](=[O:13])[C:10]([CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:27]2[NH:28][C:29]3[C:34]([C:26]=2[CH2:25][C:24]([NH:37][C:38](=[O:40])[CH3:39])([CH3:23])[CH3:36])=[CH:33][CH:32]=[C:31]([CH3:35])[CH:30]=3)=[C:11]1[OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 685807212-Benzyl-2-methyl-cyclobutane-1,3-dioneHCID 68580747N-[1,1-dimethyl-2-(6-methyl-1H-indol-3-yl)-ethyl]-acetamide

Product 1

HCID 59264916N-(2-{2-[(3-Benzyl-2-hydroxy-3-methyl-4-oxo-cyclobut-1-enyl)-phenyl-methyl]-6-methyl-1H-indol-3-yl}-1,1-dimethyl-ethyl)-acetamide

Procedure

Using general procedure C, 2-benzyl-2-methyl-cyclobutane-1,3-dione (Lit. 1) was reacted with benzaldehyde and N-[1,1-dimethyl-2-(6-methyl-1H-indol-3-yl)-ethyl]-acetamide (from Example 1.2) to give the title compound as a red solid. MS: 519.5 ([M−H]−).

Sources & evidence

ORD record
ord-c621a3af995646a8a3fed08da4353e02
Source dataset
uspto-grants-2010_04
Patent number
US07705034B2

Reaction notes

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