Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | ethyl 1-[(4-{3-[(methoxyacetyl)amino]phenyl}-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate | HCID 58127684 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66939428 | HCID 66939428 | 67% |
Reaction Steps
Under a nitrogen atmosphere at 0° C., to a solution (2 mL) of sodium hydride (60% in mineral oil, 93 mg, 2.3 mmol) in N,N-dimethylformamide was added dropwise a solution (2 mL) of the compound (720 mg, 1.8 mmol) obtained in Example 26b in tetrahydrofuran, and the mixture was stirred at room temperature for 30 min. Then, iodomethane (0.22 mL, 3.6 mmol) was added to the reaction mixture and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-ethyl acetate) to give the title compound (500 mg, 67%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08461348B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-fae246070395444dab8960606010e75e |
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| Source note | uspto-grants-2013_06 |
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