Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Pyrosulfite | HCID 656671 | — |
| Reactant | Potassium peroxymonosulphate | HCID 10313463 | — |
| Reactant | 2-(4-chlorophenyl)-N-[5-({7-[(methylthio)methyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}carbonyl)pyridin-3-yl]acetamide | HCID 70817747 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 70817269 | HCID 70817269 | 17% |
Reaction Steps
Potassium peroxomonosulfate (Oxone, 67.2 mg, 0.110 mmol) was added to a stirring solution of 2-(4-chlorophenyl)-N-[5-({7-[(methylthio)methyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}carbonyl)pyridin-3-yl]acetamide (Example 313, 25.0 mg, 0.055 mmol) in methanol (1.0 mL) and water (0.25 mL) at 0° C. After 1 hour, the reaction was allowed to warm to room temperature and stirred for 24 hours. The reaction mixture was cooled to 0° C. and sodium metabisulfite (0.5M, 1 ml) was added. The reaction mixture was evaporated under reduced pressure to remove the methanol. Water (3 mL) was added to the mixture and it was extracted with EtOAc (3×5 mL). The combined organic fractions were washed with water (5 mL), brine (5 mL), dried over magnesium sulfate the solvent was removed under reduced pressure to give the crude product as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08846698B2 |
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| Source dataset | uspto-grants-2014_09 |
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| ORD ID | ord-dca3888232fc470baebefdccf15e9cb9 |
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| Source note | uspto-grants-2014_09 |
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