Triethylamine → HCID 22637148, compound

HRID 2416030Notes

Reaction equation

HRID 2416030 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][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].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>[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][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH:4][C:32]([NH: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)=[O:34]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 112212234-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline

Product 1

HCID 22637148HCID 22637148, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent3×

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (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 thereto, 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 23 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-8b55dcb45a5d46e480277eb149cbef75
Source dataset
uspto-grants-2004_11
Patent number
US06821987B2

Reaction notes

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