Triethylamine → HCID 23118580, compound

HRID 1348837Notes

Reaction equation

HRID 1348837 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][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([F:23])[CH:17]=1.C(N(CC)CC)C.Cl[C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:43][C:44]1[S:45][CH:46]=[C:47]([CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])[N:48]=1>C(Cl)(Cl)Cl.O>[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][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:32]([NH:43][C:44]2[S:45][CH:46]=[C:47]([CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])[N:48]=2)=[O:34])=[C:18]([F:23])[CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 23118580HCID 23118580, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent3×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (30 mg) was dissolved in chloroform (3 ml) to prepare a solution. Triethylamine (0.3 ml) and a solution of triphosgene (27 mg) in chloroform (0.2 ml) were then added to the solution, and the mixture was stirred at room temperature for 30 min. Next, a solution of ethyl (2-amino-4-thiazolyl)acetate (76 mg) in chloroform (0.6 ml) 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 extract was washed with saturated brine and was dried over anhydrous sodium sulfate. The organic layer was concentrated under the reduced pressure, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give 22 mg of the title compound.

Workup

  1. customto prepare a solution
  2. stirringthe mixture was further stirred at room temperature overnight
  3. extractionthe mixture was subjected to separatory extraction with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationThe organic layer was concentrated under the reduced pressure
  7. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c1eb3f57594f4d9b9412a0d144995e9e
Source dataset
uspto-grants-2007_05
Patent number
US07211587B2

Reaction notes

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