Triethylamine → HCID 22637131, compound

HRID 1348823Notes

Reaction equation

HRID 1348823 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)[NH2:5].C(N(CC)CC)C.Cl[C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:43][C:44]1[O:48][N:47]=[C:46]([CH3:49])[CH:45]=1>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:32]([NH:43][C:44]2[O:48][N:47]=[C:46]([CH3:49])[CH:45]=2)=[O:34])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 845905-Amino-3-methylisoxazoleHCID 94429TriphosgeneHCID 218905643-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]aniline

Product 1

HCID 22637131HCID 22637131, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

3-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]aniline (84 mg) was dissolved in chloroform (2.5 ml) and triethylamine (0.25 ml) to prepare a solution. A solution of triphosgene (38 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 5 min. Next, 5-amino-3-methylisoxazole (27 mg) was added thereto, and the mixture was further stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was subjected to separatory extraction with chloroform. The organic layer was concentrated and was evaporated to dryness. Diethyl ether was added to the resultant solid, and the solid was collected by filtration and was further washed with methyl alcohol to give the title compound (34.2 mg, yield 30%).

Workup

  1. stirringthe mixture was further stirred at room temperature overnight
  2. extractionthe mixture was subjected to separatory extraction with chloroform
  3. concentrationThe organic layer was concentrated
  4. customwas evaporated to dryness
  5. additionDiethyl ether was added to the resultant solid
  6. filtrationthe solid was collected by filtration
  7. washwas further washed with methyl alcohol

Sources & evidence

ORD record
ord-8349442b06ba4e56922d5a775bcf5a6a
Source dataset
uspto-grants-2007_05
Patent number
US07211587B2

Reaction notes

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