Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2,2,2-Trifluoroethyl trifluoromethanesulfonate | HCID 80366 | — |
| Reactant | HCID 178492656 | HCID 178492656 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67465600 | HCID 67465600 | — |
Reaction Steps
A mixture of 6-{[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazole-3-carbonyl]-amino}-5-methyl-2H-indazole-7-carboxylic acid isopropylamide (500 mg, 1.07 mmol) and NaH (60%) (67 mg, 1.6 mmol) in THF (5 mL) was stirred for 1 hour at ambient temperature, and was treated with 2,2,2-trifluoroethyl trifluoromethanesulfonate (246 mg, 1.06 mmol). The resulting reaction mixture was stirred for 4 hours at 60° C. AcOEt and water was added. The phases were separated. The aqueous layer was extracted with AcOEt. The organic layers were washed with water, combined, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash-chromatography (SiO2, Toluene/AcOEt 7:3) afforded the title compound as a colorless crystalline solid. M.p. 178-181° C., LC/MS: 550 (M+H)+, 572/574 (M+Na)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08598078B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-55752f7d5c38475790832794425c6bbc |
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| Source note | uspto-grants-2013_12 |
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