Triphosgene → N-(2,4-Difluorobenzyl)-N'-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-2-fluorophenyl}urea

HRID 1375847Notes

Reaction equation

HRID 1375847 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])=[C:18]([F:23])[CH:17]=1.ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[F:36][C:37]1[CH:44]=[C:43]([F:45])[CH:42]=[CH:41][C:38]=1[CH2:39][NH2:40]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[F:36][C:37]1[CH:44]=[C:43]([F:45])[CH:42]=[CH:41][C:38]=1[CH2:39][NH:40][C:28]([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][C:18]=1[F:23])=[O:34]

Participants

6

Reactant 3

HCID 94429TriphosgeneHCID 27332442,4-DifluorobenzylamineHCID 218902744-((6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline

Product 1

HCID 22667167N-(2,4-Difluorobenzyl)-N'-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-2-fluorophenyl}ureaYield 26%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.3 ml), and a solution of triphosgene (47 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 2,4-difluorobenzylamine (28 μl) was added to the reaction solution, and the mixture was further stirred at room temperature overnight. The precipitated crystal was collected by filtration and was washed to give 20 mg (yield 26%) of the title compound.

Workup

  1. stirringthe mixture was further stirred at room temperature overnight
  2. filtrationThe precipitated crystal was collected by filtration
  3. washwas washed

Sources & evidence

ORD record
ord-fe4e17a619d6493fb1d2bd9b963f52a5
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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