2-Methylterephthalic acid → N-{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}-(4-methoxycarbonylphenyl)carboxamide

HRID 1857150Notes

Reaction equation

HRID 1857150 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.C[C:24]1[CH:32]=[C:31]([C:33]([OH:35])=[O:34])[CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=O.Cl.[CH2:37](N=C=NCCCN(C)C)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:26]([C:25]2[CH:24]=[CH:32][C:31]([C:33]([O:35][CH3:37])=[O:34])=[CH:30][CH:29]=2)=[O:28])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 2280862-Methylterephthalic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132633N-{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}-(4-methoxycarbonylphenyl)carboxamideYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (100 mg) and commercially available monomethylterephthalic acid (130 mg) were dissolved in N,N-dimethylformamide (4 ml), 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (227 mg) was added, and the admixture was stirred at room temperature for 18 hours. The reaction mixture was then purified in the same manner as described in Example 51 to obtain 99 mg of the title compound (yield: 64%).

Workup

  1. customThe reaction mixture was then purified in the same manner

Sources & evidence

ORD record
ord-0087767f0f144aa888556ad8510f7e9c
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

Loading…