Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tert-Butylamine | HCID 6385 | — |
| 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 70664982 | HCID 70664982 | 51.7% |
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 mg, 1.26 mmol) and 2-methylpropan-2-amine (461.3 mg, 6.32 mmol) with stirring overnight at 90° C. in an oil bath. The reaction mixture was cooled to room temperature, diluted with H2O (150 mL), extracted with ethyl acetate (3×80 mL). The organic layers were combined, dried over magnesium sulfate, and concentrated in vacuo to give the residue, which was purified by silica gel column chromatography (1% ethyl acetate in petroleum ether) to afford methyl 3-(tert-butylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a light yellow solid (115 mg, 51%).
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-8cd9658c0d0044968c27cfa34db4b0eb |
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| Source note | uspto-grants-2014_12 |
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