Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 68818972 | HCID 68818972 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68817395 | HCID 68817395 | 87.3% |
Reaction Steps
To a stirred solution of 325.5 mg (0.64 mmol) of tert-butyl cis-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxylate in 4 mL of N,N-dimethylformamide was added 353.8 mg of potassium carbonate, followed by 184.9 mg (1.28 mmol) of iodomethane. The suspension was stirred at room temperature overnight. After removal of the volatile material, 80 mL of ethyl acetate was added. The organic phase was washed with water and saturated sodium chloride solution, and dried over magnesium sulfate. The residue was chromatographed on silica gel eluting with ethyl acetate/hexane (3:7) to give 292.1 mg of tert-butyl cis-6-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxylate in 87% yield. MS: 523.1 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07595327B2 |
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| Source dataset | uspto-grants-2009_09 |
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| ORD ID | ord-d78230c6440447a5808eaca645a85772 |
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| Source note | uspto-grants-2009_09 |
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