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CAS No. : | 112984-60-8 | MDL No. : | MFCD00882994 |
Formula : | C16H16FN3O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SUXQDLLXIBLQHW-UHFFFAOYSA-N |
M.W : | 349.38 | Pubchem ID : | 124225 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Stage #1: at 80 - 85℃; for 1 h; Stage #2: With acetic acid In water at 20℃; for 1 h; |
Ethyl-6-fluoro-1 -methyl-4-oxo-7-(1 -piperazinyl)-4H-(1 ,3)-thiazeto-[3,2-a]-quinoline-3- carboxylate (100 gms, 0.265 moles) was stirred in water (600 ml) at 25-30°C. To this potassium hydroxide solution (50 gms of potassium hydroxide flakes is dissolved in 200 ml of water) was added and the reaction mass was heated to 80-85°C. The contents were stirred for 1 hour and after completion of reaction, the reaction mass was cooled to 25-30°C. The pH of the reaction mass was adjusted to 6.5-7.0 using 1:1 aqueous acetic acid solution. The contents were stirred at room temperature for 1 hour. The precipitated solid was filtered, washed with water (2 x 100 ml). The solid was slurried in methanol (300 ml) for 1 hour at 25-30°C, filtered, washed with methanol (2 x 50 ml) and dried under vacuum at 70-75°C to yield the title compound [90 gms, 97percent yield, 96percent HPLC purity]. |
97.3% | at 60 - 70℃; Large scale | the reaction vessel 8. 0kg a compound of formula (II), 112kg water, 6. 0kg potassium hydroxide, and heated to 60~ 70 ° C the hydrolysis reaction, 2 to 3 hours. After completion of the reaction, was cooled to room temperature, 30. 4kg washed with ethyl acetate, the aqueous layer was separated, stirred, adjusted with concentrated hydrochloric acid ρΗ 6~7, stirring was continued for 0.5 hours, the filter cake was suction filtration, an appropriate amount of ethyl washing the filter cake drying, cake was collected, 60~70 ° C hot air circulation drying, to obtain a compound of formula (III) finished 7. 36kg, yield (mol) 96.4percent, purity 97.3percent; |
90% | at 20℃; for 5 h; | 30 g of ethyl 6-fluoro-7-piperazine-1-methyl-4-oxo- [1,3] thiazepino [3,2-a] 120ml concentration of 1mol / L of potassium hydroxide solution dissolved, And stirred at room temperature for 5 hours. The solution was neutralized with a 20percent (v/v) acetic acid solution and the pH was adjusted to 7-8 and stirred well. The precipitate was collected by filtration, and the precipitate was washed three times with deionized water and acetonitrile, respectively. The precipitate was then dried in vacuo at 60 ° C to give 6-fluoro-7-piperazine-1-methyl-4-oxo- [1,3] thiazacyclo [3,2-a] 3-carboxylic acid 29g, 90percent yield. The obtained 6-fluoro-7-piperazine-1-methyl-4-oxo- [1,3] thiazepino [3,2-a] quinoline-3-carboxylic acid was 99.1percent pure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | at 20℃; for 5 h; | Take step 1)Collected ethyl 6‐fluoro‐1‐methyl‐4‐oxo‐7‐(piperazin‐1‐yl)‐1H,4H‐[1,3]thiazeto[3,2‐a]quinoline‐3‐carboxylate 30g,Dissolve in 120ml of 1mol/L potassium hydroxide solution.And stirred at room temperature for 5 hours.The solution was neutralized with a 20percent (v/v) acetic acid solution and the pH was adjusted to 7-8 and stirred well.Filter, collect the precipitate,The precipitates were washed three times with deionized water and acetonitrile, respectively.The precipitate is then vacuum dried at 60°C.Namely, 6‐fluoro‐1‐methyl‐4‐oxo‐7‐(piperazin‐1‐yl)‐1H,4H‐[1,3]thiazeto[3,2‐a]quinoline‐3‐carboxylic acid 29g, yield 90percent .The purity of the obtained 6‐fluoro‐1‐methyl‐4‐oxo‐7‐(piperazin‐1‐yl)‐1H,4H‐[1,3]thiazeto[3,2‐a]quinoline‐3‐carboxylic acid was 99.1percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.4% | With potassium hydrogencarbonate In N,N-dimethyl-formamide at 0℃; for 5 h; Large scale | the reaction vessel in step (3) obtained in prulifloxacin crude acetonitrile and 358L stirred heated to reflux to dissolve transparent, coolish, adding 0. 05kg charcoal, keep stirring under reflux for 30 minutes, filtered hot and the filtrate was natural cooled to room temperature and crystallization, through chilled water cooling crystallization overnight, centrifugation, washing the filter cake with a small amount of acetonitrile frozen crystal, drying, 80 ° C and dried under vacuum to dryness to give prulifloxacin finished 8. 73kg, yield (mole ) 92.4percent, purity 99.5percent 7. 0kg adding the compound of formula (III) in a reaction vessel, 2. 31kg potassium bicarbonate and 42L N, N- dimethylformamide, cooling down to 4 ° C, was added dropwise at a concentration of 0. 6kg / L of formula ( V) DMF solution of compound 12. 3L, controlling the internal temperature 4 ° C, dropwise Bi, 4 ° C with stirring, and the reaction time was 5.5 hours, the reaction solution was poured into ice water with stirring, and stirred for 0.5 hours, the crystals were collected by filtration, the filter cake washed with water until neutral, drained, 60~70 ° C hot air circulation drying, a compound of formula (I) prulifloxacin crude 9. 34kg, yield (moles) 96.8 percent, purity 92.6percent; (4) was added to the reaction vessel in step (3) obtained in prulifloxacin crude acetonitrile and 358L stirred heated to reflux to dissolve transparent, coolish, adding 0. 05kg activated carbon, insulation was stirred at reflux for 30 minutes, filtered hot and the filtrate cooled to room temperature crystallization, crystallization through the chilled water cooling overnight, centrifugation, washing the filter cake with a small amount of acetonitrile frozen crystal, drying, 80 ° C under vacuum to dryness to give Cape Lu Lisha star finished 8. 94kg, yield (mol) of 95.4percent, a purity of 99.7percent |
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