Triethylamine → Tivozanib
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[CH:48]=[C:47]([CH3:49])[O:46][N:45]=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[CH:48]=[C:47]([CH3:49])[O:46][N:45]=1)=[O:34]Participants
Procedure
2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (100 mg) was dissolved in chloroform (5 ml) and triethylamine (0.5 ml) to prepare a solution. A solution of triphosgene (100 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 15 min. Next, 3-amino-5-methylisoxazole (38 mg) was added thereto, and the mixture was further stirred at room temperature overnight. Distilled water was added to the reaction solution, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine and was dried over sodium sulfate. The organic layer was concentrated under the reduced pressure, and the residue was purified by HPLC using chloroform/acetone for development to give 78 mg of the title compound.
Workup
- stirringthe mixture was further stirred at room temperature overnight
- extractionthe mixture was subjected to separatory extraction with chloroform
- washThe organic layer was washed with saturated brine
- dry with materialwas dried over sodium sulfate
- concentrationThe organic layer was concentrated under the reduced pressure
- customthe residue was purified by HPLC
Sources & evidence
- ORD record
- ord-ca8348f6ee0f49d0bbb84e87b1b6504b
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07211587B2
Reaction notes
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