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(1S,6S)-2,8-diazabicyclo[4.3.0]nonane
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
Stage #1: C14H11F2NO4 With isobutylamine; copper dichloride In methanol; ethylene glycol at 50℃; for 4h; Inert atmosphere; Stage #2: (1S,6S)-2,8-diazabicyclo[4.3.0]nonane In methanol; ethylene glycol for 5h; Reflux; | 88.3% |
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: tetrachloromethane; magnesium / ethanol; toluene / 55 - 60 °C 1.2: 2 h / 30 - 35 °C 2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; water / 10 h / 100 - 110 °C 3.1: 110 - 120 °C 4.1: dichloromethane / 0 - 40 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 75 - 80 °C 6.1: zinc(II) chloride / 2 h / 110 - 115 °C 6.2: 85 - 115 °C 7.1: triethylamine / acetonitrile / 3 h / 20 - 95 °C 8.1: sodium hydroxide / 80 - 85 °C View Scheme |
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide at 80 - 85℃; | 58 g |
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; water / 10 h / 100 - 110 °C 2.1: 110 - 120 °C 3.1: dichloromethane / 0 - 40 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 75 - 80 °C 5.1: zinc(II) chloride / 2 h / 110 - 115 °C 5.2: 85 - 115 °C 6.1: triethylamine / acetonitrile / 3 h / 20 - 95 °C 7.1: sodium hydroxide / 80 - 85 °C View Scheme |
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 110 - 120 °C 2.1: dichloromethane / 0 - 40 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 75 - 80 °C 4.1: zinc(II) chloride / 2 h / 110 - 115 °C 4.2: 85 - 115 °C 5.1: triethylamine / acetonitrile / 3 h / 20 - 95 °C 6.1: sodium hydroxide / 80 - 85 °C View Scheme |
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: dichloromethane / 0 - 40 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 75 - 80 °C 3.1: zinc(II) chloride / 2 h / 110 - 115 °C 3.2: 85 - 115 °C 4.1: triethylamine / acetonitrile / 3 h / 20 - 95 °C 5.1: sodium hydroxide / 80 - 85 °C View Scheme |
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 75 - 80 °C 2.1: zinc(II) chloride / 2 h / 110 - 115 °C 2.2: 85 - 115 °C 3.1: triethylamine / acetonitrile / 3 h / 20 - 95 °C 4.1: sodium hydroxide / 80 - 85 °C View Scheme |
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: zinc(II) chloride / 2 h / 110 - 115 °C 1.2: 85 - 115 °C 2.1: triethylamine / acetonitrile / 3 h / 20 - 95 °C 3.1: sodium hydroxide / 80 - 85 °C View Scheme |
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 3 h / 20 - 95 °C 2: sodium hydroxide / 80 - 85 °C View Scheme |
2,3,4-trifluoro-5-methoxybenzoic acid
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: N,N-dimethyl-formamide; thionyl chloride / 2.5 h / 90 - 95 °C 2.1: tetrachloromethane; magnesium / ethanol; toluene / 55 - 60 °C 2.2: 2 h / 30 - 35 °C 3.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; water / 10 h / 100 - 110 °C 4.1: 110 - 120 °C 5.1: dichloromethane / 0 - 40 °C 6.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 75 - 80 °C 7.1: zinc(II) chloride / 2 h / 110 - 115 °C 7.2: 85 - 115 °C 8.1: triethylamine / acetonitrile / 3 h / 20 - 95 °C 9.1: sodium hydroxide / 80 - 85 °C View Scheme |
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
sodium methylate
C22H27N3O5
Conditions | Yield |
---|---|
With dimethyl sulfoxide at 110 - 145℃; Temperature; | 81% |
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