P-Anisidine → 7-methoxy-N-(4-methoxyphenyl)benzofuran-2-carboxamide

HRID 1057921Notes

Reaction equation

HRID 1057921 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.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1>>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][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:19][CH:18]=1

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 6060377-Methoxy-1-benzofuran-2-carboxylic acid

Product 1

HCID 227338677-methoxy-N-(4-methoxyphenyl)benzofuran-2-carboxamide

Procedure

Substantially the same procedure as in Example 219 was repeated using a starting material, 7-methoxybenzofuran-2-carboxylic acid, and p-anisidine to give N-(4-methoxyphenyl)-7-methoxybenzofuran-2-carboxamide (Compound 399a). Successively, it was formylated to give N-(4-methoxyphenyl)-4-formyl-7-methoxybenzofuran-2-carboxamide (Compound 399b), then compound 399b was reacted with cyclobutylamine to give compound 399 as a white solid.

Sources & evidence

ORD record
ord-9e1b0347386f4b0789b32bbddbc23a8a
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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