4-Chloroaniline → N-(4-chlorophenyl)-7-methoxybenzofuran-2-carboxamide

HRID 1057919Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([C:12]([OH:14])=O)=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:12]([C:9]2[O:10][C:11]3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=3[CH:8]=2)=[O:14])=[CH:18][CH:17]=1

Participants

Reactant 2

HCID 78124-Chloroaniline

HCID 6060377-Methoxy-1-benzofuran-2-carboxylic acid

Product 1

HCID 22734372N-(4-chlorophenyl)-7-methoxybenzofuran-2-carboxamide

Procedure

Substantially the same procedure as in Example 219 was repeated using a starting material, 7-methoxybenzofuran-2-carboxylic acid, and 4-chloroaniline to give N-(4-chlorophenyl)-7-methoxybenzofuran-2-carboxamide (Compound 379a). Successively, it was formylated to give N-(4-chloropheny)-4-formyl-7-methoxybenzofuran-2-carboxamide (Compound 379b), then compound 379b was reacted with cyclobutylamine to give compound 379 as a white solid.

Sources & evidence

ORD record: ord-61932a9d646348bf8cb340863748d424
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06514996B2

Reaction notes

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