Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-butyl N-(pyrrolidin-3-yl)carbamate | HCID 2757234 | — |
| Reactant | HCID 23364547 | HCID 23364547 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 14774111 | HCID 14774111 | 87.3% |
Reaction Steps
A solution of 0.40 g (1.00 mmol) of ethyl 6,7,8-trifluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.22 g (1.18 mmol) of 3-t-butoxycarbonylaminopyrrolidine, 0.30 g (3.00 mmol) of triethylamine, and 15 ml of acetonitrile was refluxed for 18 hours. The mixture was cooled and concentrated. The residue was dissolved in 10 ml of 6N hydrochloric acid, refluxed for three hours, and cooled to room temperature. The solids were filtered, washed with water and ether, and suspended in water. The suspension was made basic (pH 12) and filtered through a fiberglass pad, and the filtrate was neutralized to pH 6.7. The solids were filtered and washed with water and ether to give 0.38 g of the title compound, mp 230°-232° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04920120 |
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| Source dataset | uspto-grants-1990_04 |
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| ORD ID | ord-03b999c13e7a479ca161e33aae91b47e |
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| Source note | uspto-grants-1990_04 |
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