Water → N-{[4-(6-Carbamoyl-7-methoxy-4-quinolyl)oxyl-2-fluorophenyl]}-N'-(4-fluorophenyl)-N-methylurea

HRID 853543Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][CH:8]=[C:7]2Cl)(=[O:3])[NH2:2].[F:17][C:18]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:19]=1[N:25]([CH3:36])[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)=[O:27].[H-].[Na+].O>CS(C)=O>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][CH:8]=[C:7]2[O:24][C:22]1[CH:21]=[CH:20][C:19]([N:25]([CH3:36])[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[O:27])=[C:18]([F:17])[CH:23]=1)(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 85 °C

Procedure

6-Carbamoyl-4-chloro-7-methoxyquinoline (41 mg, 0.1744 mmol) and N-(2-fluoro-4-hydroxyphenyl)-N′-(4-fluorophenyl)-N-methylurea (57 mg, 0.2048 mmol) were dissolved in dimethylsulfoxide (1.0 ml), and then sodium hydride (8.4 mg, 0.2093 mmol) was added and the mixture was heated and stirred at 85° C. for 30 minutes. After cooling the reaction solution to room temperature, water was added and the precipitated crystals were filtered out. The crystals were then suspended in acetone: diethyl ether=1:2 and refiltered out, washed with diethyl ether and dried by aspiration to obtain the title compound (46 mg, 0.0961 mmol, 55.13%) as yellow crystals.

Workup

temperaturethe mixture was heated
temperatureAfter cooling the reaction solution to room temperature
filtrationthe precipitated crystals were filtered out
washwashed with diethyl ether
customdried by aspiration

Sources & evidence

ORD record: ord-5a5ebc2232f24a29972e4f922e744c74
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253286B2

Reaction notes

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