2,4-Difluorophenyl isocyanate → N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxy-2-fluorophenyl)-N'-(2,4-difluorophenyl)urea

HRID 1010101Notes

Reaction equation

HRID 1010101 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][C:3]=1[F:26].[F:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1[N:35]=[C:36]=[O:37]>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:24]=[CH:25][C:2]([NH:1][C:36]([NH:35][C:29]2[CH:30]=[CH:31][C:32]([F:34])=[CH:33][C:28]=2[F:27])=[O:37])=[C:3]([F:26])[CH:4]=1)#[N:18]

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 229362984-(4-Amino-3-fluorophenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline

Product 1

HCID 22936371N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxy-2-fluorophenyl)-N'-(2,4-difluorophenyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(4-Amino-3-fluorophenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline (352 mg) was suspended in toluene (20 ml) and the suspension was heated to reflux for dissolution, after which 2,4-difluorophenyl isocyanate (236 μl) was added dropwise and the mixture was heated to reflux for 30 minutes. After cooling, the precipitated solid was filtered out, washed with ether and ethyl acetate and dried to obtain 380 mg of the title compound.

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for dissolution
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 30 minutes
  5. temperatureAfter cooling
  6. filtrationthe precipitated solid was filtered out
  7. washwashed with ether and ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-bf20e2a5aeef49e68dcab1e8f906711e
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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