Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | Tivozanib | HCID 9911830 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 21079510 | HCID 21079510 | 84% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07166722B2 |
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| Source dataset | uspto-grants-2007_01 |
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| ORD ID | ord-6a6e691c251c4ac594a84e6ed26b8f6b |
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| Source note | uspto-grants-2007_01 |
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