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inquirypiperazine
ethyl 6,7-difluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 60℃; for 4h; | 87% |
In dimethyl sulfoxide at 60℃; for 4h; | 87% |
In N,N-dimethyl-formamide Ambient temperature; | 84% |
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide | |
In N,N-dimethyl-formamide at 20 - 25℃; Product distribution / selectivity; |
piperazine
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 10 - 55℃; for 9.16667h; | 74% |
3,4-difluorophenyl isothiocyanate
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) KOH / 1.) dioxane, RT, 30 min., 2.) 4 deg C, 15 h 2: 2.22 g / K2CO3 / dimethylformamide / 1 h / 70 °C 3: 0.350 g / PPE / 1.5 h / 80 °C 4: 84 percent / dimethylformamide / Ambient temperature View Scheme | |
Multi-step reaction with 6 steps 1: 1.) KOH / 1.) dioxane, RT, 30 min., 2.) 4 deg C, 15 h 2: dimethylformamide / 1.) 0 deg C, 1.5 h, 2.) RT, 2 h 3: 58 percent / diphenyl ether / 5 h / 240 °C 4: 99 percent / 35percent HCl / ethanol / 2 h / Ambient temperature 5: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C 6: 84 percent / dimethylformamide / Ambient temperature View Scheme |
ethyl 7,6-difluoro-4-hydroxy-2-mercaptoquinoline-3-carboxylate
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C 2: 84 percent / dimethylformamide / Ambient temperature View Scheme |
3,4-difluorophenyl dithiocarbamic acid triethylammonium
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: ethyl chloroformate, triethylamine / CHCl3 / 3.5 h / Ambient temperature 2: 1.) KOH / 1.) dioxane, RT, 30 min., 2.) 4 deg C, 15 h 3: 2.22 g / K2CO3 / dimethylformamide / 1 h / 70 °C 4: 0.350 g / PPE / 1.5 h / 80 °C 5: 84 percent / dimethylformamide / Ambient temperature View Scheme | |
Multi-step reaction with 7 steps 1: ethyl chloroformate, triethylamine / CHCl3 / 3.5 h / Ambient temperature 2: 1.) KOH / 1.) dioxane, RT, 30 min., 2.) 4 deg C, 15 h 3: dimethylformamide / 1.) 0 deg C, 1.5 h, 2.) RT, 2 h 4: 58 percent / diphenyl ether / 5 h / 240 °C 5: 99 percent / 35percent HCl / ethanol / 2 h / Ambient temperature 6: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C 7: 84 percent / dimethylformamide / Ambient temperature View Scheme |
ethyl 6,7-difluoro-4-hydroxy-2-<(methoxymethyl)thio>-quinoline-3-carboxylate
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 99 percent / 35percent HCl / ethanol / 2 h / Ambient temperature 2: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C 3: 84 percent / dimethylformamide / Ambient temperature View Scheme |
3-(3,4-difluorophenyl)-4-methyl<1,3>thiazetidin-2-ylidenemalonate
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.350 g / PPE / 1.5 h / 80 °C 2: 84 percent / dimethylformamide / Ambient temperature View Scheme |
diethyl<<(3,4-difluorophenyl)amino><(methoxymethyl)-thio>methylene>malonate
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 58 percent / diphenyl ether / 5 h / 240 °C 2: 99 percent / 35percent HCl / ethanol / 2 h / Ambient temperature 3: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C 4: 84 percent / dimethylformamide / Ambient temperature View Scheme |
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 2.22 g / K2CO3 / dimethylformamide / 1 h / 70 °C 2: 0.350 g / PPE / 1.5 h / 80 °C 3: 84 percent / dimethylformamide / Ambient temperature View Scheme | |
Multi-step reaction with 5 steps 1: dimethylformamide / 1.) 0 deg C, 1.5 h, 2.) RT, 2 h 2: 58 percent / diphenyl ether / 5 h / 240 °C 3: 99 percent / 35percent HCl / ethanol / 2 h / Ambient temperature 4: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C 5: 84 percent / dimethylformamide / Ambient temperature View Scheme |
3,4-difluoroaniline
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 0 °C 2: ethyl chloroformate, triethylamine / CHCl3 / 3.5 h / Ambient temperature 3: 1.) KOH / 1.) dioxane, RT, 30 min., 2.) 4 deg C, 15 h 4: 2.22 g / K2CO3 / dimethylformamide / 1 h / 70 °C 5: 0.350 g / PPE / 1.5 h / 80 °C 6: 84 percent / dimethylformamide / Ambient temperature View Scheme | |
Multi-step reaction with 8 steps 1: 0 °C 2: ethyl chloroformate, triethylamine / CHCl3 / 3.5 h / Ambient temperature 3: 1.) KOH / 1.) dioxane, RT, 30 min., 2.) 4 deg C, 15 h 4: dimethylformamide / 1.) 0 deg C, 1.5 h, 2.) RT, 2 h 5: 58 percent / diphenyl ether / 5 h / 240 °C 6: 99 percent / 35percent HCl / ethanol / 2 h / Ambient temperature 7: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C 8: 84 percent / dimethylformamide / Ambient temperature View Scheme |
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
ulifloxacin
Conditions | Yield |
---|---|
Stage #1: ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate With water; potassium hydroxide at 80 - 85℃; for 1h; Stage #2: With acetic acid In water at 20℃; for 1h; pH=6.5 - 7; | 97% |
With water; potassium hydroxide at 60 - 70℃; Large scale; | 97.3% |
With potassium hydroxide at 20℃; for 5h; | 90% |
With potassium hydroxide In water; tert-butyl alcohol at 50 - 60℃; for 1h; | 88% |
Stage #1: ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate With water; potassium hydroxide; tert-butyl alcohol at 20 - 60℃; Stage #2: With water; acetic acid In tert-butyl alcohol |
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
1-bromoacetone
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 4h; | 67% |
With potassium carbonate In N,N-dimethyl-formamide |
4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide for 1h; Ambient temperature; | 66% |
With potassium hydrogencarbonate In N,N-dimethyl-formamide |
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C 2: 18 percent / K2CO3 / dimethylformamide / 3 h / 60 - 80 °C View Scheme |
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
prulifloxacin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C 2: 62 percent / KHCO3 / dimethylformamide / 5 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / 1 h / 80 - 85 °C 1.2: 1 h / 20 °C / pH 6.5 - 7 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.17 h / 20 °C 2.2: 21 h / 10 - 30 °C View Scheme |
4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one
ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one; ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate With triethylamine In N,N-dimethyl-formamide at 0 - 5℃; Stage #2: With hydrogenchloride In methanol; dichloromethane at 0 - 5℃; Product distribution / selectivity; |
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