Triethylamine → HCID 22667155, compound

HRID 1008406Notes

Reaction equation

HRID 1008406 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.CN[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1.C(=O)([O-])O.[Na+].[CH2:49]([N:51](CC)CC)[CH3:50]>C(Cl)(Cl)Cl>[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:51][CH2:49][CH2:50][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1)=[O:34]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 207272-Pyridinamine, N-methyl-HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 218898992-Chloro-4-((6,7-dimethoxyquinazolin-4-yl)oxy)aniline

Product 1

HCID 22667155HCID 22667155, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

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-(methylamino)pyridine (19 μl) was added to the reaction solution, and the mixture was stirred at 60° C. for additional one hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by HPLC by development with chloroform/methanol to give 26 mg (yield 37%) of the title compound.

Workup

  1. stirringthe mixture was stirred at 60° C. for additional one hr
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by HPLC by development with chloroform/methanol

Sources & evidence

ORD record
ord-a39cb0a1e09f40faa944b4c84abc5b7a
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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