Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N~1~-(Pyridin-2-yl)ethane-1,2-diamine | HCID 410428 | — |
| Reactant | HCID 59002994 | HCID 59002994 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 59002978 | HCID 59002978 | 55% |
Reaction Steps
A mixture of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-methylamino-4-oxoquinoline-3-carboxylic acid (500 mg, 1.54 mmol), N-2-pyridyl-1,2-ethanediamine (423 mg, 3.03 mmol) and triethylamine (0.430 mL, 3.09 mmol) in anhydrous DMSO (8 mL) was stirred at 100° C. for 3 h. After cooling, the reaction mixture was poured into ice-water (50 mL) and extracted with EtOAc (2×100 mL). The organic layers were combined, washed with water, dried over Na2SO4, and evaporated. The residue was purified by column chromatography (hexane: EtOAc 1:1→EtOAc) to give 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-5-methylamino-7-[2-(2-pyridylamino)ethylamino]-4-oxoquinoline-3-carboxylic acid (373 mg, 55%) as a yellow 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-636356477ae14f42818560a3fbde2414 |
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| Source note | uspto-grants-2011_11 |
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