HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,8-Diazabicyclo(5.4.0)undec-7-ene → 10-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 8,9-Difluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid | HCID 534278 | — |
| Reactant | 2,5-Diazabicyclo(2.2.2)octane dihydrochloride | HCID 22924390 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 10-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid | HCID 13565840 | 26.8% |
Reaction Steps
A solution of 0.56 g (2.0 mmol) of 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 0.41 g (2.2 mmol) of 2,5-diazabicyclo[2.2.2]octane dihydrochloride, 0.90 ml (6.0 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 25 ml of acetonitrile was heated under reflux for 18 hours. The solution was evaporated to dryness and the residue was triturated with methanol and filtered to give 0.20 g of the title compound, 260°-265° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04571396 |
| Source dataset | uspto-grants-1986_02 |
| ORD ID | ord-004445253279438d81facaf8f68fee8b |
| Source note | uspto-grants-1986_02 |