Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 121393736 | HCID 121393736 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 121393761 | HCID 121393761 | 48.2% |
Reaction Steps
Sodium hydride (12 mg of a 60% dispersion in mineral oil, 0.30 mmol) was added to a solution of 4-(5-{5-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazol-4-yl}-1H-pyrazol-1-yl)benzonitrile (Example 1) (94 mg, 0.23 mmol) in DMF (1.5 mL) under a nitrogen atmosphere. The mixture was stirred for 5 minutes and the resultant yellow solution was treated with methanesulfonyl chloride (32 mg, 21.4 μL, 0.28 mmol). The mixture was stirred for 2 h then treated with water and extracted with EtOAc. The organic phase was washed with water and brine then dried (sodium sulfate) and concentrated in vacuo. T he residue was purified by chromatography using silica gel eluting with 25%-60% ethyl acetate in cyclohexane. The product thus obtained was freeze-dried from acetonitrile-water to afford the title compound (54 mg) a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09409870B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-81a8592db18049d0b427e4b89e61f09d |
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| Source note | uspto-grants-2016_08 |
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