Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 53831072 | HCID 53831072 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86757279 | HCID 86757279 | 87.7% |
Reaction Steps
7-Methoxynaphthalene-2-sulfonic acid [1-(2-chloro-quinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide (0.4 g, 0.81 mmol), prepared as in EXAMPLE 15, Part F, is dissolved in DMF (20 mL) and cooled to 0° C. To the solution is added methyl iodide (0.28 g, 2.01 mmol) and sodium hydride (34 mg, 0.85 mmol, 60% mineral oil dispersion). The ice water bath is removed and the mixture is stirred at room temperature for 3 hours. The resulting solution is poured into a separatory funnel and diluted with EtOAc (100 mL). The organic layer is washed with 1N HCl, H2O and saturated NaCl. The organic phase is then dried over MgSO4, filtered and concentrated. The crude residue is purified by column chromatography eluting with 10% EtOAc/CH2Cl2 to give the title compound (0.36 g, 0.71 mmol) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06281227B1 |
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| Source dataset | uspto-grants-2001_08 |
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| ORD ID | ord-8f26e2d376234b4e8647b7f444728406 |
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| Source note | uspto-grants-2001_08 |
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