Triphosgene → HCID 22667164, compound

HRID 1375837Notes

Reaction equation

HRID 1375837 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 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 temperature for additional 30 min
  2. filtrationThe precipitated crystal was collected by filtration
  3. washwas washed

Sources & evidence

ORD record
ord-6e9500ce49a74f1ab6824dbc4ede52ff
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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