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Water → HCID 21079510, compound

HRID 1375168
Notes
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Reaction equation

HRID 1375168 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:23][C:24]([NH:26][C:27]1[CH:31]=[C:30]([CH3:32])[O:29][N:28]=1)=[O:25].O.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1.O>C(#N)C.CO>[C:34]1([CH3:44])[CH:35]=[CH:36][C:37]([S:40]([OH:43])(=[O:41])=[O:42])=[CH:38][CH:39]=1.[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:23][C:24]([NH:26][C:27]1[CH:31]=[C:30]([CH3:32])[O:29][N:28]=1)=[O:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 9911830Tivozanib

Product 1

HCID 21079510HCID 21079510, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342
Acetonitrile
Solvent
2×

Procedure

N-{2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N′-(5-methyl-3-isoxazolyl)urea (2.0 g) produced in Production Example was added to acetonitrile (27 mL), a solution of p-toluenesulfonic acid monohydrate (2.5 g) in acetonitrile (27 mL) was added dropwise thereto, and the mixture was stirred at room temperature for 3 hr. The resultant precipitate was collected by filtration and the filtered product was then dried under the reduced pressure. The powder thus obtained was stirred in methanol (70 mL) and water (40 mL) under reflux for complete dissolution. The solution was then cooled to room temperature and was stirred at that temperature overnight. The resultant precipitate was filtered, and the filtered product was then dried under the reduced pressure to give a form I crystal of N-{2-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N′-(5-methyl-3-isoxazolyl)urea p-toluenesulfonate (2.3 g, yield 84.0%).

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. customthe filtered product was then dried under the reduced pressure
  3. customThe powder thus obtained
  4. temperatureThe solution was then cooled to room temperature
  5. stirringwas stirred at that temperature overnight
  6. filtrationThe resultant precipitate was filtered
  7. customthe filtered product was then dried under the reduced pressure

Sources & evidence

ORD record
ord-6a6e691c251c4ac594a84e6ed26b8f6b
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07166722B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes