HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(5-Acetamidomethyl-2-isoindolinyl)-1-cyclopropyl-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 | 1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | HCID 535414 | — |
| Reactant | 5-Acetamidomethylisoindoline hydrobromide | HCID 19828513 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 7-(5-Acetamidomethyl-2-isoindolinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | HCID 57151875 | 34% |
Reaction Steps
283 mg of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 325 mg of 5-acetamidomethylisoindoline hydrobromide, 536 mg of DBU, and 2 ml of anhydrous DMF were processed in the same manner as in Example 20 to produce 154 mg of 7-(5-acetamidomethyl-2-isoindolinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. 1H-NMR (CDCl3) δ: 8.74 (1H, s, C2 --H), 7.89 (1H, d, J=14Hz, C5 --H), 7.26-7.30 (3H, brs, ARM-H), 5.15 (4H, brs, 2 x --CH2N--), 4.47 (2H, d, J=6Hz, CH2NH2), 4.00 (1H, m, ##STR310## 2.06 (3H, s, --COCH3), 1.17-1.31 (4H, m, ##STR311##
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05026856 |
| Source dataset | uspto-grants-1991_06 |
| ORD ID | ord-99ce4f7888c94f15ac54f56feb3fbf5c |
| Source note | uspto-grants-1991_06 |