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Quality Control of [ 112984-60-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 112984-60-8 ]

SDS Specification

Alternatived Products of [ 112984-60-8 ]

Product Details of [ 112984-60-8 ]

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 :		Chemical Name :	6-Fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

Safety of [ 112984-60-8 ]

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:

Application In Synthesis of [ 112984-60-8 ]

* 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.

Upstream synthesis route of [ 112984-60-8 ]
Downstream synthetic route of [ 112984-60-8 ]

[ 112984-60-8 ] Synthesis Path-Upstream 1~4

1
[ 80715-22-6 ]
[ 112984-60-8 ]
[ 123447-62-1 ]

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

Reference： [1] Patent: CN103113392, 2016, B, . Location in patent: Paragraph 0044; 0058; 0059; 0060
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 25, p. 4727 - 4738
[3] Patent: WO2008/59512, 2008, A1, . Location in patent: Page/Page column 8
[4] Patent: WO2008/111016, 2008, A1, . Location in patent: Page/Page column 5
[5] Patent: WO2012/1357, 2012, A1, . Location in patent: Page/Page column 22-23

2
[ 80841-78-7 ]
[ 112984-60-8 ]
[ 123447-62-1 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 11, p. 1872 - 1877

3
[ 80715-22-6 ]
[ 112984-60-8 ]
[ 123447-62-1 ]
[ 156834-57-0 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 5, p. 1419 - 1426

4
[ 80715-22-6 ]
[ 112984-60-8 ]
[ 123447-62-1 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 11, p. 1872 - 1877

[ 112984-60-8 ] Synthesis Path-Downstream 1~1

1
[ 113028-17-4 ]
[ 112984-60-8 ]

Yield	Reaction Conditions	Operation in experiment
97%		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 25-30C. 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 80-85C. The contents were stirred for 1 hour and after completion of reaction, the reaction mass was cooled to 25-30C. 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 25-30C, filtered, washed with methanol (2 x 50 ml) and dried under vacuum at 70-75C to yield the title compound [90 gms, 97% yield, 96% HPLC purity].
97.3%	With water; potassium hydroxide; 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 rhoEta 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) 96.4%, purity 97.3%;
90%	With potassium hydroxide; at 20℃; for 5h;	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 20% (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, 90% yield. The obtained 6-fluoro-7-piperazine-1-methyl-4-oxo- [1,3] thiazepino [3,2-a] quinoline-3-carboxylic acid was 99.1% pure.

Example 8: Preparation of Ulifloxacin;Tertiary butanol (5.55It), 6-fluoro-l-methyl-4-oxo-7-(l-piperazinyl)-4H-[l,3]thiazeto [3,2- a]quinoline-3-carboxylic acid ethyl ester (1.1 lkg), potassium hydroxide (0.37kg) and water (2.75 It) were added at room temperature. The reaction mixture was heated to 600C and maintained for 1.5 hours. Reaction completion was checked by TLC. This was followed by the addition of water (22.2 It) and acetic acid (0.39 It). The reaction mixture was filtered, washed with water followed by slurry wash with acetone (2.22 It) twice and dried to obtain 0.95 kg of ulifloxacin having purity 97.56% by HPLC.

Reference： [1]Patent: WO2012/1357,2012,A1 .Location in patent: Page/Page column 22
[2]Patent: CN103113392,2016,B .Location in patent: Paragraph 0024; 0037; 0038; 0039
[3]Patent: CN107383069,2017,A .Location in patent: Paragraph 0063; 0064
[4]Journal of Medicinal Chemistry,1992,vol. 35,p. 4727 - 4738
[5]Patent: WO2009/93268,2009,A1 .Location in patent: Page/Page column 15

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Technical Information

? Alkyl Halide Occurrence ? Arndt-Eistert Homologation ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hunsdiecker-Borodin Reaction ? Hydride Reductions ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Preparation of Carboxylic Acids ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Carboxylic Acids ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 112984-60-8 ] {[proInfo.proName]}

Quality Control of [ 112984-60-8 ]

Related Doc. of [ 112984-60-8 ]

Product Details of [ 112984-60-8 ]

Safety of [ 112984-60-8 ]

Application In Synthesis of [ 112984-60-8 ]

[ 112984-60-8 ] Synthesis Path-Upstream 1~4

[ 112984-60-8 ] Synthesis Path-Downstream 1~1

Technical Information

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Fluorinated Building Blocks

Ketones

Carboxylic Acids

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Other Aromatic Heterocycles

Piperazines

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Prevention

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Environmental hazards

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[ 112984-60-8 ]

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[ 112984-60-8 ]