1-Adamantanecarboxylic acid → N-{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}adamantanecarboxamide

HRID 1857154Notes

Reaction equation

HRID 1857154 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]12([C:33](O)=[O:34])[CH2:32][CH:27]3[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]3)[CH2:24]1)[CH2:30]2.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:33]([C:23]23[CH2:32][CH:27]4[CH2:26][CH:25]([CH2:31][CH:29]([CH2:28]4)[CH2:30]2)[CH2:24]3)=[O:34])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 132351-Adamantanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132799N-{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}adamantanecarboxamideYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (51 mg) and commercially available adamantanecarboxylic acid (110 mg) were dissolved in N,N-dimethylformamide (2 ml), 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (107 mg) was added, and the admixture was stirred at room temperature for 15 hours. The reaction mixture was purified in the same manner as described in Example 51 to obtain 13 mg of the title compound (yield: 17%).

Workup

  1. customThe reaction mixture was purified in the same manner

Sources & evidence

ORD record
ord-35adf090ba5c42118d879394b0f4994a
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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