P-Anisidine → 3-(4-Methoxybenzoyl)amino-N-(4-methoxyphenyl)-2-indolecarboxamide

HRID 1355629Notes

Reaction equation

HRID 1355629 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH3:10][O:11][C:12]1[CH:32]=[CH:31][C:15]([C:16]([NH:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:28](O)=[O:29])=[O:17])=[CH:14][CH:13]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:28]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:29])=[O:17])=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 7732P-AnisidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 120695493-(4-Methoxybenzoyl)amino-2-indolecarboxylic acid

Product 1

HCID 159085653-(4-Methoxybenzoyl)amino-N-(4-methoxyphenyl)-2-indolecarboxamideYield 14.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution p-anisidine (79 mg, 0.645 mmol) in methylene chloride (5 mL) was added 3-(4-methoxybenzoyl)amino-2-indolecarboxylic acid (200 mg, 0.645 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (247 mg, 1.29 mmol), and 4-dimethylaminopyridine (8.0 mg, 0.065 mmol). The resulting solution was stirred at room temperature for 6 h. The resulting precipitate was collected via vacuum filtration to provide 38 mg (14%) of the title compound as a white solid.

Workup

  1. filtrationThe resulting precipitate was collected via vacuum filtration

Sources & evidence

ORD record
ord-ea68df5daac349e185019f1ba29715da
Source dataset
uspto-grants-2003_07
Patent number
US06586459B2

Reaction notes

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