4-Fluorophenyl isocyanate → N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N'-(4-fluorophenyl)urea

HRID 387702Notes

Reaction equation

HRID 387702 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1>C1(C)C=CC=CC=1>[C:17]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:19][CH2:20][CH2:21][O:22][CH3:23])[N:10]=[CH:9][CH:8]=[C:7]2[O:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:34]([NH:33][C:30]2[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=2)=[O:35])=[CH:25][CH:24]=1)#[N:18]

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 229365064-(4-Aminophenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline

Product 1

HCID 10116220N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N'-(4-fluorophenyl)ureaYield 96.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(4-Aminophenoxy)-7-(2-methoxyethoxy)-6-cyanoquinoline (109 mg, 0.325 mmol) was dissolved in toluene (5 ml) while heating, and then 4-fluorophenyl isocyanate (0.057 ml, 0.488 mmol) was added and the mixture was heated to reflux for 1 hour. After cooling, the precipitated crystals were filtered out, washed with ethyl acetate and dried under reduced pressure to obtain the title compound (148 mg, 0.311 mmol, 96.4%) as white crystals.

Workup

  1. temperaturewhile heating
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1 hour
  4. temperatureAfter cooling
  5. filtrationthe precipitated crystals were filtered out
  6. washwashed with ethyl acetate
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c5aff11bc9e440329c1c933d97f437f6
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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