Triethylamine → Ki-20227

HRID 1817454Notes

Reaction equation

HRID 1817454 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]([O:23][CH3:24])[CH:17]=1.C(N(CC)CC)C.ClC(Cl)(O[C:36](=[O:42])OC(Cl)(Cl)Cl)Cl.[S:44]1[CH:48]=[CH:47][N:46]=[C:45]1[CH:49]([NH2:51])[CH3:50]>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:36]([NH:51][CH:49]([C:45]2[S:44][CH:48]=[CH:47][N:46]=2)[CH3:50])=[O:42])=[C:18]([O:23][CH3:24])[CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 198969851-(1,3-Thiazol-2-yl)ethan-1-amineHCID 218910314-((6,7-Dimethoxyquinolin-4-yl)oxy)-2-methoxyaniline

Product 1

HCID 9869779Ki-20227Yield 144.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent3×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-methoxyaniline (816 mg) was dissolved in chloroform (40 ml) and triethylamine (2.0 ml) to prepare a solution. A solution of triphosgene (368 mg) in chloroform (1.0 ml) was then added to the solution, and the mixture was stirred at room temperature for one hr. Next, a solution of 1-(1,3-thiazol-2-yl)-1-ethylamine (352 mg) in chloroform (1.0 ml) was added thereto, and the mixture was stirred at room temperature overnight. Water (40 ml) was added thereto, and the mixture was stirred for 10 min, followed by extraction with chloroform. The organic layer was washed with saturated brine and was dried over sodium sulfate. The solvent was removed by evaporation, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (860 mg, 72%).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. stirringthe mixture was stirred for 10 min
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialwas dried over sodium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-bf53e52bd87842938aea537518b4ce1b
Source dataset
uspto-grants-2009_10
Patent number
US07598258B2

Reaction notes

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