Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclohexylamine | HCID 7965 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate | HCID 77231184 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 70665078 | HCID 70665078 | 83.7% |
Reaction Steps
To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (200 mg, 0.63 mmol) in DMSO (10 mL) was added DIEA (163.3 mg, 1.27 mmol) and cyclohexanamine (250.7 mg, 2.53 mmol), and the reaction was allowed to proceed with stirring overnight at 90° C. in an oil bath. The reaction mixture was cooled down to room temperature and diluted with water (150 mL). The mixture was extracted with ethyl acetate (3×80 mL), the organic layers combined and dried over magnesium sulfate, concentrated in vacuo to give the residue, which was purified by a silica gel column chromatography (1% ethyl acetate in petroleum ether) to afford methyl 3-(cyclohexylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a light yellow solid (200 mg, 83%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08912188B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-a6bac91bed0e452aa1e48b2ce56c2f8c |
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| Source note | uspto-grants-2014_12 |
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