Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 46897742 | HCID 46897742 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59448303 | HCID 59448303 | 62.2% |
Reaction Steps
{(3S,4S)-3-(3,4-Dichloro-phenyl)-4-[(5-trifluoromethyl-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-yl}-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone (30.0 mg, 0.051 mmol) were dissolved in DMF (1 mL) and treated with NaH (55% dispersion in oil) (2.5 mg, 0.056 mmol) at ambient temperature. After 5 min methyl iodide (3.5 μL, 0.056 mmol) were added and the reaction mixture was stirred over night. After quenching with water and extraction with ethyl acetate (3×10 mL) the combined organic phases were dried on sodium sulfate and filtered. After evaporation of the solvent the crude product was subjected to column chromatography (silica gel, ethyl acetate) to yield the title product (19 mg, 62%) as a colorless foam. ES-MS m/e: 598.3 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08318759B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-6bcec36617754f9e82140f7e262236df |
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| Source note | uspto-grants-2012_11 |
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