2,4-Difluorophenyl isocyanate → 1-(2,4-Difluorophenyl)-3-(4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl)urea

HRID 1008397Notes

Reaction equation

HRID 1008397 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][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[N:31]=[C:32]=[O:33]>C(Cl)(Cl)Cl>[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[NH:31][C:32]([NH:20][C:19]1[CH:21]=[CH:22][C:16]([O:15][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][N:7]=2)=[CH:17][CH:18]=1)=[O:33]

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)aniline

Product 1

HCID 226671011-(2,4-Difluorophenyl)-3-(4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl)ureaYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in chloroform (3 ml), and 2,4-difluorophenyl isocyanate (24 μl) was then added to the solution. The mixture was heated under reflux overnight. The precipitated crystal was collected by filtration and was washed to give 55 mg (yield 72%) of the title compound. 1H-NMR (DMSO-d6, 400 MHz): δ 3.98 (s, 3H), 3.99 (s, 3H), 7.04-7.08 (m, 2H), 7.24 (d, J=8.8 Hz, 2H), 7.29-7.35 (m, 1H), 7.38 (s, 1H), 7.54 (d, J=9.0 Hz, 2H), 7.56 (s, 1H), 8.06-8.14 (m, 1H), 8.51-8.54 (m, 1H), 8.54 (s, 1H), 9.11-9.12 (m, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationThe precipitated crystal was collected by filtration
  4. washwas washed

Sources & evidence

ORD record
ord-09908b8fd277451dad1c6c4577930dcc
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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