Triphosgene → HCID 22667164, compound

HRID 1008405Notes

Reaction equation

HRID 1008405 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].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>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:5][C:3]=1[NH:4][C:28]([NH:40][CH2:39][C:38]1[CH:41]=[CH:42][C:43]([F:45])=[CH:44][C:37]=1[F:36])=[O:34]

Participants

6

Reactant 3

HCID 94429TriphosgeneHCID 27332442,4-DifluorobenzylamineHCID 218898992-Chloro-4-((6,7-dimethoxyquinazolin-4-yl)oxy)aniline

Product 1

HCID 22667164HCID 22667164, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline (50 mg) was dissolved in chloroform (5 ml) and triethylamine (1 ml), and a solution of triphosgene (45 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 2,4-difluorobenzylamine (22 μl) was added to the reaction solution, and the mixture was stirred at room 10 temperature for additional 30 min. The precipitated crystal was collected by filtration and was washed to give 48 mg (yield 64%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room 10 temperature for additional 30 min
  2. filtrationThe precipitated crystal was collected by filtration
  3. washwas washed

Sources & evidence

ORD record
ord-0c5d054f1ade474a96776e6c0d04d591
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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