Toluene → N-(4-[(7-cyano-6-methoxy-4-quinolyl)oxy]phenyl)-N'-(4-fluorophenyl)urea

HRID 387959Notes

Reaction equation

HRID 387959 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16]=[O:17])=[CH:11][CH:10]=1.[NH2:18][C:19]1[CH:39]=[CH:38][C:22]([O:23][C:24]2[C:33]3[C:28](=[CH:29][C:30]([C:36]#[N:37])=[C:31]([O:34][CH3:35])[CH:32]=3)[N:27]=[CH:26][CH:25]=2)=[CH:21][CH:20]=1>C(#N)C>[C:36]([C:30]1[CH:29]=[C:28]2[C:33]([C:24]([O:23][C:22]3[CH:38]=[CH:39][C:19]([NH:18][C:16]([NH:15][C:12]4[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=4)=[O:17])=[CH:20][CH:21]=3)=[CH:25][CH:26]=[N:27]2)=[CH:32][C:31]=1[O:34][CH3:35])#[N:37]

Participants

5

Reactant 3

HCID 1140TolueneHCID 709554-Fluorophenyl isocyanateHCID 22936943HCID 22936943, compound

Product 1

HCID 67204014N-(4-[(7-cyano-6-methoxy-4-quinolyl)oxy]phenyl)-N'-(4-fluorophenyl)urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After adding toluene (5 ml), acetonitrile (1.5 ml) and 4-fluorophenyl isocyanate (0.105 ml) to 4-(4-aminophenoxy)-6-methoxyquinoline-7-carbonitrile (180 mg), the mixture was heated to reflux for 30 minutes. The mixture was cooled, and the precipitated crystals were filtered out and washed with toluene to obtain the title compound (230 mg) as light yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperatureThe mixture was cooled
  4. filtrationthe precipitated crystals were filtered out
  5. washwashed with toluene

Sources & evidence

ORD record
ord-29e0e94f7edf4d658e6f3db149d5272b
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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