Dimethylformamide → 4-Butyl-N-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}benzamide

HRID 1857143Notes

Reaction equation

HRID 1857143 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]([O:31]CCCC)(=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.C(N=C=N[CH2:42][CH2:43][CH2:44]N(C)C)C.[CH3:48]N(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:23]([C:24]2[CH:25]=[CH:26][C:27]([CH2:48][CH2:44][CH2:43][CH3:42])=[CH:28][CH:29]=2)=[O:31])=[CH:20][CH:21]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8698Butyl BenzoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 221326434-Butyl-N-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}benzamideYield 78%

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (54 mg) and commercially available 4-butyl benzoate (54 mg) were dissolved in N,N-dimethylformamide (2 ml), 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (85 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 51 to obtain 65 mg of the title compound (yield: 78%).

Workup

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

Sources & evidence

ORD record
ord-a5a9620c2d724310934731bdbea64d57
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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