4-Acetylbenzoic Acid → 4-Acetyl-N-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}benzamide

HRID 1857142Notes

Reaction equation

HRID 1857142 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:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1)(=[O:25])[CH3:24].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:30]([C:29]2[CH:33]=[CH:34][C:26]([C:23](=[O:25])[CH3:24])=[CH:27][CH:28]=2)=[O:31])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 114704-Acetylbenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 221327524-Acetyl-N-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}benzamideYield 53.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (54 mg) and commercially available 4-acetylbenzoic acid (46 mg) were dissolved in N,N-dimethylformamide (2 ml), 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (87 mg) was added, and the admixture was stirred at room temperature for 22 hours. The reaction mixture was then purified in the same manner as described in Example 50 to obtain 43 mg of the title compound (yield: 53%).

Workup

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

Sources & evidence

ORD record
ord-4c675a2f902149449046c3e48e6aad16
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

Loading…