Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | 5-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | HCID 10566894 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59003015 | HCID 59003015 | 97.6% |
Reaction Steps
To a suspension of 5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (4.97 g, 16.0 mmol) in DMF (200 mL), triethylamine (3.35 mL, 24.0 mmol) and ethyl chloroformate (1.84 mL, 19.2 mmol) were added. After stirring at 0° C. for 2 h., 25% aq. NH3 (5 mL) was added and the mixture was stirred at room temperature for 3 h. The reaction mixture was poured into water (1.5 L) and the resulting precipitate was collected by filtration, washed with water and dried to give 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxamide (4.83 g, 97%) as a pale brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08063221B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-50199a42d6154f019d7e71419073d900 |
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| Source note | uspto-grants-2011_11 |
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