Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 5-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | HCID 10566894 | — |
| Reactant | N-(((3R,4S)-4-Fluoropyrrolidin-3-yl)methyl)cyclopropanamine | HCID 11147857 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 66705229 | HCID 66705229 | 68.6% |
Reaction Steps
5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (250 mg), (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine (190 mg), triethylamine (0.17 mL) and dimethylsulfoxide (4 mL) were mixed together. The mixture was stirred at 100° C. for 9 hours and was subsequently concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: dichloromethane: methanol=40:1). The eluted yellow solid was recrystallized from ethanol to give 5-amino-1-cyclopropyl-7-[(3S,4S)-3-cyclopropylaminomethyl-4-fluoro-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid as yellow crystals (248 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08106072B2 |
|---|
| Source dataset | uspto-grants-2012_01 |
|---|
| ORD ID | ord-7cb982f2cc314329aa6056183b8e63f6 |
|---|
| Source note | uspto-grants-2012_01 |
|---|
