HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 7-(7-Tert-butoxycarbonylamino-5-azaspiro[2,4]heptane-5-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 8-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | HCID 9835941 | — |
| Reactant | Tert-butyl 5-azaspiro[2.4]heptan-7-ylcarbamate | HCID 14930995 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 7-(7-Tert-butoxycarbonylamino-5-azaspiro[2,4]heptane-5-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | HCID 22417087 | 74.6% |
Reaction Steps
200 mg of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 150 mg of compound 11 and 70 mg of triethylamine were added to 5 ml of acetonitrile and the mixture was refluxed for 24 hours. After cooling, the solvent was removed under reduced pressure and to the residue was added water. The precipitate was collected by filtration and washed successively with water, acetonitrile, ethanol and ether and dried. The procedure gave 245 mg of 7-(7-tert-butoxycarbonylamino-5-azaspiro[2.4]heptan-5-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid melting at 205°-207° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05508428 |
| Source dataset | uspto-grants-1996_04 |
| ORD ID | ord-b919883338b64989982d6b5267aa8ecf |
| Source note | uspto-grants-1996_04 |