Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Chloromethyl Methyl Ether | HCID 7864 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 15950608 | HCID 15950608 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86629853 | HCID 86629853 | 88% |
Reaction Steps
Sodium hydride (32 mg, 60%, 0.8 mmol) was suspended in tetrahydrofuran (10 ml), and a solution of N-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,5-dimethyl-3-trifluoromethylpyrazole-4-carboxamide (250 mg, 0.48 mmol) in tetrahydrofuran (5 ml) was added dropwise. After stirring at room temperature for 30 min, a solution of chloromethyl methyl ether (64 mg, 0.8 mmol) in tetrahydrofuran (2 ml) was added and the mixture was stirred for 5 hr. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the desired compound (238 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08404861B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-be73b56f4f9f450f816d44d6de725f63 |
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| Source note | uspto-grants-2013_03 |
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