Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | N-(5-bromo-2-morpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine | HCID 59631101 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59631098 | HCID 59631098 | — |
Reaction Steps
To a stirred solution of N-(5-bromo-2-morpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine (described herein) (18.0 mg, 0.035 mmol) in N,N-dimethylformamide (2 mL) was added 60% sodium hydride (2.11 mg, 0.053 mmol), followed by iodomethane (7.5 mg, 0.053 mmol). Stirring continued for 1.5 h. Water was added to quench the reaction and the resulting mixture was extracted with EtOAc (3×10 mL). The combined organic layers was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (0-60% EtOAc/hexanes) to give N-(5-bromo-2-morpholinopyridin-3-yl)-5,7-difluoro-N,3-dimethyl-2-(pyridin-2-yl)quinolin-4-amine as a yellow foam. Mass Spectrum (ESI) m/e=526.2, (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08940724B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-e39391a80cce45898bb4132a4309eb60 |
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| Source note | uspto-grants-2015_01 |
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