4-Bromobenzoic acid → 4-Bromo-N-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}benzamide

HRID 1857149Notes

Reaction equation

HRID 1857149 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.[Br:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=1.Cl.C(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:28]([C:27]2[CH:31]=[CH:32][C:24]([Br:23])=[CH:25][CH:26]=2)=[O:29])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 114644-Bromobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 221327034-Bromo-N-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}benzamideYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (52 mg) and commercially available 4-bromobenzoic acid (78 mg) were dissolved in N,N-dimethylformamide (2 ml), 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (102 mg) was added, and the admixture was stirred at room temperature for 17 hours. The reaction mixture was then purified in the same manner as described in Example 51 to obtain 43 mg of the title compound (yield: 52%).

Workup

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

Sources & evidence

ORD record
ord-aee4e7a5e83b4e9a95d60407a1ff14e9
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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