Structure of 112811-71-9
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CAS No. : | 112811-71-9 |
Formula : | C16H15F2NO4 |
M.W : | 323.29 |
SMILES Code : | O=C(C1=CN(C2CC2)C3=C(C=C(F)C(F)=C3OC)C1=O)OCC |
MDL No. : | MFCD05864419 |
InChI Key : | XPAOPAPDCRLMTR-UHFFFAOYSA-N |
Pubchem ID : | 10758239 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
89.78% | Stage #1: at 90 - 100℃; for 3 h; Stage #2: With triethylamine In acetonitrile at 20℃; for 0.5 h; |
In a 2000 mL three-necked round-bottomed flask, 150.00 g of acetic anhydride was added, stirred, heated to 80 °C,boric acid 28. 00g, stirring evenly, slowly warming to 110 °C, stirring reaction 2 hours. Cooled to 60-70 ° C, ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate 100 was added. And the reaction was continued at 90 to 100 °C for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature. 650 mL of acetonitrile and 592 mL of triethylamine were added to the reaction solution, and the mixture was stirred for 30 minutes. To the reaction solution was added 39.39 g of (S, S) -2,8-diazabicyclo [4.3.0] nonane (1.01eq), heating reflux reaction 3 hours, TLC detection reaction is completed, down to room temperature, stirring 30 minutes, ice bath temperature 5 ~ 10 °C 90mL concentrated hydrochloric acid, adjust PH = 1. 2, continue ice bath Stirring and crystallization for 8 hours, filtration, ice-ethanol 50mLX2 washing filter cake, filter cake 50 ~ 60 ° C / _0.095MPa vacuum drying 12 hours to obtain crude moxifloxacin hydrochloride 121. 48g light yellow powder, yield: 89 78percent, HPLC: 99.7percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.8 - 96.6% | With tetrafluoroboric acid; In water; at 30 - 100℃; for 5h; | Example-1 : Preparation of Gatifloxacin with isolation of interme- diate (boron difluoride chelate derivative) Stage-1 : Preparation of L-CYCLOPROPYL-6, 7-DIFLUORO-8-METHOXY-4-OXO- 1,4-dihydro-3-quinoline carboxylic acid boron difluoride chelate. Ethyl-l-cyclopropyl-6, 7-DIFLUORO-8-METHOXY-4-OXO-1, 4-dihydro-3- quinoline carboxylate (100G) is suspended in 40% AQ. hydrofluoroboric ACID (1000 ML). TEMPERATUR. E OF the reaction mass is raised and maintained at 95C to 100C for 5hrs followed by cooling to 30C- 35C. Water (400 ml) is added and maintained at 25C-30C for 2hrs. Product is filtered, washed with water (500 ml) and dried at 40C-45C to constant weight. Dry weight of the product: 101.6 g (Yield: 95.8 %); EXAMPLE-11 : Preparation of Gatifloxacin without isolation of intermediate (boron difluoride chelate derivative) Stage-1 : Preparation of L-CYCLOPROPYL-6, 7-difluoro-8-methoxy-4- oxo-1, 4-dihydro-3-quinoline carboxylic acid boron difluoride chelate. Ethyll-cyclopropyl-6, 7-difluoro-8-methoxy-4-oxo-1, 4-dihydro-3- quinoline carboxylate (lOOg) is suspended in 40% aq. hydrofluoroboric acid (1000 ml). Temperature of the reaction mass is raised and maintained at 95C to 100C for 5 hrs followed by cooling to 30C-35C. 400 ml DM water is added, maintained at 25C - 30C for 2hrs. The product is filtered, washed with DM water (500 ML) and dried at 40C-45C to constant weight. The dry wt is 102.5 g (Yield: 96.6 %) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron trifluoride diethyl etherate; In tetrahydrofuran; at 70℃; for 18h; | To a solution of compound 5 (3.01 g, 9.3 mmol) in anhydrous THF (40 ml), was added boron trifluoroetherate (19.76g, 17.6 ml, 139.2 mmol). The solution was heated at 70 C for 18 h. A precipitate formed. The solution was allowed to cool partially before diethyl ether (30 ml) was added. The solution was then allowed to cool further to RT. The precipitate was collected by filtration, washed with diethyl ether and dried under reduced pressure at 45 C for 2 h, giving compound 6 (1.73 g). ¹H NMR No. [(CD3)2SO] 9.18 (s, 1 H), 8.26 (dd, J=9.7,8.2 Hz, 1 H), 4.52 (m, 1 H), 4.18 (d, J=2.2 Hz, 3H), 1.32 (m, 4H). LCMS (APCI+) 344. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.83% | With hydrogenchloride; In methanol; water; at 65℃; for 15h; | Reaction: In a 250 mL round bottom flask, add 10 g of the compound of formula 2 and 100 mL of anhydrous methanol, stir and mix slowly, then add 13.3 mL of 36% hydrochloric acid slowly. The addition is complete; the system is heated to 65 C., and the reaction is stirred at this temperature. 15h; Post-treatment: After the reaction is over, the system is cooled to 10 C., and the crystals are stirred for 2 h. The system is filtered under reduced pressure. The filter cake is washed with 20 mL of anhydrous methanol, and then vacuum-dried at 60 C. for 8 h to obtain 8.86 g of formula 3. The compound shown, yield: 96.83%; |
With hydrogenchloride; sodium hydroxide; In methanol; | PREPARATION 6 1-Cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (IIc) [Step (E13)] 10 ml of a 4% w/v aqueous solution of sodium hydroxide were added to a solution of 0.48 g (0.0015 mole) of ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (XXXII) (prepared as described in Preparation 3) in 20 ml of methanol, and the mixture was allowed to stand at room temperature for 5 hours. The reaction mixture was then acidified by adding concentrated hydrochloric acid to precipitate a crystalline substance, which was collected by filtration to afford 0.34 g of 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (IIC) as colorless powdery crystals melting at 184-185 C. Mass Spectrum: m/e 295 (M+), 251 (M+ -CO2). Elemental analysis: Calculated for C14 H11 F2 NO4: C, 56.95%; H, 3.76%; N, 4.75%. Found: C, 56.90%; H, 3.84%; N, 4.56%. | |
With sulfuric acid; water; acetic acid; for 2h;Heating / reflux; | Ethyl-l-cyclopropyl-1, 4-dihydro-6,7-difluoro-8-methoxy-4-oxo-quinoline-3-carboxylate (28.6 g, 88 mmol) is suspended in a mixture of acetic acid, water, sulfuric acid [(8/6/1,] 300 mL) and is refluxed for 2 hours. The reaction mixture is cooled at [0C] and the desired product is collected by filtration. |
With sulfuric acid; water; In acetic acid; for 1h; | Analysis (%) for C16 H15 F2 NO4; Calcd. (Found): C, 59.44 (59.34); H, 4.68 (4.59); N, 4.33 (4.33). To these crystals (4.5 g) was added a mixed solution of acetic acid (30 ml), concentrated sulfuric acid (4 ml) and water (22 ml), and the mixture was refluxed for 1 hour. After cooling, ice water (100 ml) was added and the resulting precipitate was collected by filtration, washed with water and then dried to give title compound (4 g) as colorless powder, mp 185-186 C. Analysis (%) for C14 H11 F2 NO4; Calcd. (Found): C, 56.95 (56.68); H, 3.76 (3.70); N, 4.74 (4.74). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.2% | EXAMPLE-I Stage-1 : Preparation of L-CYCLOPROPYL-6, 7-difluoro-8-methoxy-4-oxo- 1, 4-dihydro-3-quinoline carboxylic ACID-03, 04) bis (ACYLOXY-O) borate Acetic anhydride (175 g) is heated to 70C and boric acid (30 g) is slowly added lot wise in a temperature range of 70C to 90C. The temperature is then raised, maintained under reflux for 1 hr followed by cooling to about 70C. Ethyl-l-cyclopropyl-6, 7-DIFLUORO-8-METHOXY-4- oxo-1,4-dihydro-3-quinoline carboxylate (100 g) is added under stirring. The temperature is then raised and maintained for 1 hr in the range of 100C to 105C. The reaction mass is cooled to 0C, chilled water (400 ml) is added slowly followed by cold water (600 ml) at temperature 0C to 5C and maintained for 2 hrs at 0C to 5C. The product which is a boron acetate complex is filtered, washed with water (500 ml) and dried at 55C to 60C under vacuum to constant weight. The dry wt is 130.0 g corresponding to yield of 95. 2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; ethanol; water; dimethyl sulfoxide; | EXAMPLE 34 1-Cyclopropyl-6-fluoro-7-[3S-(1,2,3-triazol-1-yl)pyrrolidin-1-yl]-8-methoxy-1,4-dihydro-4-oxoquinoline -3-carboxylic acid To 50 mg (0.15 mmol) of <strong>[112811-71-9]ethyl 6,7-difluoro-1-cyclopropyl-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate</strong> was added 1 ml of fluoroboric acid (50% in water) and the mixture was heated at 90-100 C. for 3 hr. The solution was then poured into water and solid collected (60 mg). The white solid was dissolved in 1 ml of DMSO and to this solution was added 52 mg (0.3 mmol) of 3S-(1,2,3-triazol-1-yl)pyrrolidine hydrochloride and 46 mg (0.3 mmol) of DBU. The mixture was then heated at 90 C. for 42 hr. The reaction mixture was cooled to room temperature and water was added and solid collected. This solid was dissolved in 8 ml of 80% methanol and 0.25 ml of triethylamine was added and refluxed for 4 hr. The solution was cooled and the few particles were filtered. The supernatant was evaporated to dryness, and ethanol was added to the residue, the solid collected, washed with ether and dried to yield 10 mg of the desired product, m.p. 195-197 C. 1 H NMR (TFA) delta: 9.34 (s, 1H), 8.68 (s, 1H), 8.57 (d, 1H), 8.09 (d, 13.2Hz, 1H), 5.95-5.8 (m, 1H), 4.85-4.3 (m, 4H), 4.2-4.0 (m, 1H), 3.79 (s, 3H), 3.1-2.7 (m, 2H), 1.7-1.1 (m, 4H). |
Tags: 112811-71-9 synthesis path| 112811-71-9 SDS| 112811-71-9 COA| 112811-71-9 purity| 112811-71-9 application| 112811-71-9 NMR| 112811-71-9 COA| 112811-71-9 structure
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H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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