N-(2-Aminophenyl)-4-methoxybenzamide → HCID 21352766, compound

HRID 427658

Reaction equation

HRID 427658 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][C:10]2[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([C:28](O)=[O:29])=[CH:25][C:24]=2[CH:31]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:28]([C:26]3[O:27][C:23]4[CH:22]=[CH:21][C:20]([Cl:19])=[CH:31][C:24]=4[CH:25]=3)=[O:29])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 785232N-(2-Aminophenyl)-4-methoxybenzamideHCID 9378385-Chloro-1-benzofuran-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 21352766HCID 21352766, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N1-(4-methoxybenzoyl)-1,2-benzenediamine (200 mg, 0.826 mmol) in methylene chloride (5 mL) was added 5-chlorobenzofuran-2-carboxylic acid (162 mg, 0.826 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (316 mg, 1.65 mmol), and 4-dimethylaminopyridine (10 mg, 0.083 mmol). The resulting solution was stirred at room temperature for 6 h. The resulting precipitate was collected via vacuum filtration to provide 209 mg (60%) of the title compound as an amorphous off-white solid.

Workup

  1. filtrationThe resulting precipitate was collected via vacuum filtration

Sources & evidence

ORD record
ord-8d514fc1701949409f497721456c7de0
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Linked notes

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