HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Amino-1-cyclopropyl-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | HCID 13910947 | — |
| Reactant | 1,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole dihydrobromide | HCID 23282849 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 5-Amino-1-cyclopropyl-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | HCID 9952225 | 57.6% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
0.4 g of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 0.8 g of 3,7-diazabicyclo[3.3.0]oct-1(5)-ene dihydrobromide and 0.6 ml of 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) were suspended in 40 ml of acetonitrile and the suspension was refluxed in 100° C. oil bath for 7 hours. The reaction mixture was kept overnight at room temperature. The produced precipitate was filtered and washed with methanol. 0.3 g of the titled compound was obtained (yield 57%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05091384 |
| Source dataset | uspto-grants-1992_02 |
| ORD ID | ord-32757052a0f24ddc93c994f1cb6dbc6e |
| Source note | uspto-grants-1992_02 |