Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N~1~-(Pyridin-2-yl)ethane-1,2-diamine | HCID 410428 | — |
| Reactant | HCID 59002884 | HCID 59002884 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 59002849 | HCID 59002849 | 42.4% |
Reaction Steps
A mixture of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-5-(trifluoroacetamido) quinoline-3-carbonitrile (500 mg, 1.29 mmol), N-2-pyridyl-1,2-ethanediamine (354 mg, 2.58 mmol) and triethylamine (0.36 mL, 2.58 mmol) in anhydrous DMSO (8 mL) was stirred at 60° C. for 16 h. After cooling, the reaction mixture was poured into ice-water (50 mL). The resulting precipitate was collected by filtration, washed with water and then dried. The crude product was purified by column chromatography (Hexane:EtOAc 1:1→2:3→EtOAc→CH2Cl2: MeOH 8:1) to give 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-[2-(2-pyridylamino)ethylamino]-5-(trifluoroacetamido)quinoline-3-carbonitrile (276 mg, 42%) as a brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08063221B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-27b6371cc0cb42b8847f470e96d086d4 |
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| Source note | uspto-grants-2011_11 |
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