Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Cyclopropyl-6,7-difluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | HCID 14651254 | — |
| Reactant | tert-Butyl [(3-methylpyrrolidin-3-yl)methyl]carbamate | HCID 15129218 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 14774121 | HCID 14774121 | 74.9% |
Reaction Steps
A mixture of 0.61 g (2.18 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.56 g (2.61 mmol) of 3-[(t-butoxycarbonyl)aminomethyl]-3-methylpyrrolidine, 0.66 g (6.54 mmol) of triethylamine, and 25 mL of acetonitrile was refluxed for 6 hours, then stirred overnight at room temperature. The precipitate was collected by filtration and washed with acetonitrile and ether. The crude product was suspended in 20 mL of 6N hydrochloric acid and 20 mL of glacial acetic acid and was stirred at room temperature for 3 hours. The solution was concentrated and the residue was triturated with ether. The solid was removed by filtration, washed with ether, and dried to give 0.61 g of the title compound as the hydrochloride, mp 250°-252° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05585491 |
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| Source dataset | uspto-grants-1996_12 |
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| ORD ID | ord-d23f5e59a2d942a0b2a1a14dc993dfdc |
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| Source note | uspto-grants-1996_12 |
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