Participants
| Role | Name | HCID | Charge |
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| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | HCID 535414 | — |
| Reactant | HCID 20087916 | HCID 20087916 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 86748485 | HCID 86748485 | 53.2% |
Reaction Steps
A mixture of 2.6 g (9.2 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 2.57 g (11 mmol) of 3-[N-(methyl)trifluoroacetamido]-2-methylazetidine hydrochloride and 3 g (30 mmol) of triethylamine in 30 ml of pyridine is heated to reflux for 2 hours. The mixture is evaporated under vacuum, the residue is diluted with ice-cold water, the resulting mixture is filtered and the product is washed with water. 2.5 g are obtained. The product is recrystallized from acetonitrile. 2.25 g of 1-cyclopropyl-6,8-difluoro-7-{trans-3-[N-(methyl)trifluoroacetamido]-2-methyl-1-azetidinyl}-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, melting point 246°-9° C., are obtained. 1H NMR, δ,J=Hz[DMSO]; 14.1, (s, 1H); 8.6 (s, 1H); 7.75 (d, 1H, J=13 Hz); 4.5 (m, 5H); 3.2 (s, 3H). IR(KBr).-1730, 1704, 1627, 1466 cm-1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05393758 |
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| Source dataset | uspto-grants-1995_02 |
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| ORD ID | ord-aca6cfd54d9f46c7962e9b3ab256b230 |
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| Source note | uspto-grants-1995_02 |
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