110871-86-8

Basic information

• Product Name: Sparfloxacin
• Synonyms: 5-AMINO-1-CYCLOHEXYL-7-(CIS-3,5-DIMETHYLPIPERAZINO)-6,8-DIFLUORO-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID;,5-dimethyl-1-piperazinyl)-4-oxo-,cis-;at4140;ci978;Clorsulon, Vetranal;SPARFLOXACIN, [2-14C]- 5-25 MCI(185-925 MBQ)/MMOL, DELIVERED >3-Quinolinecarboxylic acid, 5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-, cis-;3-Quinolinecarboxylic acid, 5-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethyl-1-piperazinyl]-6,8-difluoro-1,4-dihydro-4-oxo-, rel- (9CI)
• CAS NO: 110871-86-8
• Molecular Formula: C₁₉H₂₂F₂N₄O₃
• Molecular Weight: 392.4
• EINECS: 1308068-626-2
• Product Categories: Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals;API's;VFEND
• Mol File: 110871-86-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 265°C
• Boiling Point: 640℃
• Flash Point: >110°(230°F)
• Appearance: white to light yellow/
• Density: 1.436 g/cm³
• Vapor Pressure: 4.2E-14mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: Store at 0-5°C
• PKA: pKa1 6.25, pKa2 9.30(at 25℃)
• Water Solubility: Soluble in DMSO at 9mg/ml. Sparingly soluble in water
• BRN: 9170271
• CAS DataBase Reference: Sparfloxacin(CAS DataBase Reference)
• NIST Chemistry Reference: Sparfloxacin(110871-86-8)
• EPA Substance Registry System: Sparfloxacin(110871-86-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: VB1986500
• Hazardous Substances Data: 110871-86-8(Hazardous Substances Data)

Usage

Description

Sparfloxacin is the most potent fluoroquinolone antibiotic introduced for the treatment of community acquired infections. It has superior and broad in vitro activity against members of family Enterobacferiaceae and anaerobic bacteria, some of which are resistant toβ-lactam antibiotics or to aminoglycosides. In patients with surgical infections, sparfloxacin shows excellent activity against resistant pathogens. It is effective in treating patients with bladder irritability and is reported to have potential in the treatment of leprosy and Mycobacterium tuberculosis in mice. Favorable pharmacokinetic properties, good intracellular penetration and a lack of transferable resistance have been reported.

Chemical Properties

Light yellow powder

Originator

Dainippon (Japan)

Uses

Different sources of media describe the Uses of 110871-86-8 differently. You can refer to the following data:
1. antifungal
2. A fluorianted quinolone antibacterial
3. A fluorianted quinolone antibacterial.

Manufacturing Process

A mixture of the known compound, ethyl pentafluorobenzoylacetate [J. Org. Chem., 35, 930 (1970)] (25 g), ethyl orthoformate (20 g), and acetic anhydride (23 g) was refluxed for 2 h. The reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in diethyl ether and allowed to react with cyclopropylamine (5.1 g) to give ethyl 2- pentafluorobenzoyl-3-cyclopropylaminoacrylate (28 g), melting point 89°C.The ethyl 2-pentafluorobenzoyl-3-cyclopropylaminoacrylate (28 g) was dissolved in dry tetrahydrofuran and allowed to react with 60% sodium hydride (3.85 g) at room temperature to give ethyl 1-cyclopropyl-5,6,7,8- tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (18.4 g), melting point 170°-171°C.A mixture of ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4- oxoquinoline-3-carboxylate (28.2 g), benzylamine (9.8 ml), anhydrous potassium carbonate (23.6 g), and acetonitrile (140 ml) was heated at 100°- 110°C for 1 h to give ethyl 5-benzylamino-1-cyclopropyl-6,7,8-trifluoro-1,4- dihydro-4-oxoquinoline-3-carboxylate (21.4 g), which was recrystallized from ethanol, melting point 134°-135°C.The ethyl 5-benzylamino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4- oxoquinoline-3-carboxylate (20 g) was dissolved in acetic acid (100 ml) and ethanol (150 ml), and hydrogenolyzed in the presence of 5% palladiumcarbon (0.5 g) to give ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro- 4-oxoquinoline-3-carboxylate (14.1 g), which was recrystallized from chloroform-ethanol, melting point 236°-237°C.A mixture of the ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4- oxoquinoline-3-carboxylate (12.6 g), acetic acid (80 ml), water (50 ml), and concentrated sulfuric acid (9 ml) was heated at 100°-110°C for 40 min to give 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (11.1 g), which was recrystallized from chloroform-ethanol, melting point 294°-295°C.A mixture of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4- oxoquinoline-3-carboxylic acid (1.25 g), cis-2,6-dimethylpiperazine (2.0 g), and dimethylformamide was stirred at room tempersture for 24 h. The reaction mixture was evaporated to dryness under reduced pressure and water was added to the residue. The mixture was extracted with chloroform and the extract was dried. After evaporation of chloroform, ethanol was added to the residue. The resulting crystals were filtered and recrystallized from chloroform-ethanol to give 5-amino-1-cyclopropyl-6,8-difluoro-7-(cis-3,5- dimethyl-1-piperazinyl)-1,4-dihydro- 4-oxoquinoline-3-carboxylic acid (1.4 g), melting point: 258°-260°C.

Brand name

Zagam (Mylan);Spara.

Therapeutic Function

Antibacterial

World Health Organization (WHO)

Sparfloxacin is a quinolone antimicrobial agent. See also under quinolone and fluoroquinolone antimicrobial agents.

Pharmaceutical Applications

It is highly active against most aerobic Grampositive cocci and Gram-negative bacilli, including fastidious Gram-negative bacilli, Acinetobacter spp., Campylobacter spp. and Legionella spp. Ps. aeruginosa is weakly susceptible. Activity also extends to the genital mycoplasmas, M. tuberculosis and M. avium complex isolates. It is moderately active against some anaerobes (including the B. fragilis group); L. monocytogenes is resistant.It is well absorbed, achieving a plasma concentration of 1–1.5 mg/L 4.5 h after a 400 mg oral dose. Absorption is decreased in the presence of antacids owing to the formation of chelates with metallic ions. Concentrations in many tissues, including lung, exceed those in plasma. The plasma half-life is 15–20 h. CSF penetration is limited. Around 5–10% of a dose is eliminated unchanged in the urine, with about 30% appearing as the glucuronide. Total clearance is 10–15 L/h. The plasma half-life increases only modestly in renal failure to 30–40 h. About 50–60% of the dose appears as unchanged drug in the feces, mainly as the glucuronide, accounting for 10–20% of the administered dose.Adverse events are those common to fluoroquinolones, in particular gastrointestinal tract disturbances, CNS effects (mainly headache and insomnia) and rashes. Photosensitivity reactions have been observed in 2–11% of patients. It can prolong the QTc interval and cases of torsade de pointes have been reported. It does not potentiate the toxicity of theophylline.It has been used for respiratory and other infections caused by susceptible bacteria, but use has been restricted in the USA and Europe because of phototoxicity and cardiotoxicity.

Clinical Use

Sparfloxacin, (cis)-5-amino-1-cyclopropyl-7-(3,5-dimethyl)-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylicacid, is a newer fluoroquinolone.This compound exhibits higher potency against Grampositivebacteria, especially staphylococci and streptococci,than the fluoroquinolones currently marketed. It is also moreactive against chlamydia and the anaerobe Bacteroides fragilis.The activity of sparfloxacin against Gram-negative bacteriais also very impressive, and it compares favorably withciprofloxacin and ofloxacin in potency against Mycoplasmaspp., Legionella spp., Mycobacteria spp., and Listeria monocytogenes.Sparfloxacin has a long elimination half-life of18 hours, which permits once-a-day dosing for most indications.The drug is widely distributed into most fluidsand tissues. Effective concentrations of sparfloxacin areachieved for the treatment of skin and soft tissue infections,lower respiratory infections (including bronchitis and bacterialpneumonias), and pelvic inflammatory disease causedby gonorrhea and chlamydia. Sparfloxacin has also beenrecommended for the treatment of bacterial gastroenteritisand cholecystitis. The oral bioavailability of sparfloxacinis claimed to be good, and sufficient unchanged drug isexcreted to be effective for the treatment of urinary tract infections.Nearly 20% of an orally administered dose is excretedas an inactive glucuronide.

InChI:InChI=1/C19H22FN3O3/c1-10-7-22(8-11(2)21-10)17-6-16-13(5-15(17)20)18(24)14(19(25)26)9-23(16)12-3-4-12/h5-6,9-12,21H,3-4,7-8H2,1-2H3,(H,25,26)

Synthetic route

5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (103772-14-1) + cis-2,6-dimethylpiperazine (21655-48-1, 1013625-96-1) → sparfloxacin (110871-86-8)

Conditions	Yield
With pyridine at 80℃; for 0.666667h;	63%
In N-methyl-acetamide

1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester (107564-02-3) → sparfloxacin (110871-86-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 79 percent / triethylamine / toluene / 1 h / Heating 2: 96 percent / acetic acid, aq. H2SO4 / 0.17 h / 100 °C 3: 63 percent / pyridine / 0.67 h / 80 °C View Scheme
Multi-step reaction with 4 steps 1: 79 percent / triethylamine / toluene / 1 h / Heating 2: 80 percent / H2 / 5percent Pd/C / acetic acid; ethanol / Ambient temperature 3: 94 percent / acetic acid, aq. H2SO4 / 0.17 h / 100 °C 4: 63 percent / pyridine / 0.67 h / 80 °C View Scheme

ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (103772-13-0) → sparfloxacin (110871-86-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / acetic acid, aq. H2SO4 / 0.17 h / 100 °C 2: 63 percent / pyridine / 0.67 h / 80 °C View Scheme

ethyl 5-(benzylamino)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate (110872-04-3) → sparfloxacin (110871-86-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / acetic acid, aq. H2SO4 / 0.17 h / 100 °C 2: 63 percent / pyridine / 0.67 h / 80 °C View Scheme
Multi-step reaction with 3 steps 1: 80 percent / H2 / 5percent Pd/C / acetic acid; ethanol / Ambient temperature 2: 94 percent / acetic acid, aq. H2SO4 / 0.17 h / 100 °C 3: 63 percent / pyridine / 0.67 h / 80 °C View Scheme

lanthanum(III) nitrate hexahydrate + sparfloxacin (110871-86-8) + rac-Ala-OH (302-72-7) → La(NO3)(sparfloxacin(1-))(DL-alanine)(H2O)*H2O

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand and DL-alanine, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	95%

sparfloxacin (110871-86-8) + C14H16ClO2P → C32H33F2N4O3P

Conditions	Yield
Stage #1: C14H16ClO2P With triethylamine In methanol for 0.666667h; Schlenk technique; Inert atmosphere; Stage #2: sparfloxacin In methanol for 0.166667h; Darkness; Schlenk technique; Inert atmosphere;	95%

gold(III) tetrachloride trihydrate + sparfloxacin (110871-86-8) → [AuCl2(sparfloxacin)]Cl.2H2O

Conditions	Yield
In methanol at 20℃; for 24h;	92%

iron(III) chloride hexahydrate + sparfloxacin (110871-86-8) + rac-Ala-OH (302-72-7) → FeCl(sparfloxacin(1-))(DL-alanine)(H2O)*H2O

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand and DL-alanine, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	89%

sparfloxacin (110871-86-8) + manganese(ll) chloride → Mn(sparfloxacin(1-))2(H2O)2

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	88%

UO2(3+)*3NO3(1-)*6H2O=UO2(NO3)3*6H2O + sparfloxacin (110871-86-8) + rac-Ala-OH (302-72-7) → UO2(sparfloxacin(1-))(DL-alanine)(H2O)

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand and DL-alanine, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	87%

lanthanum(III) nitrate hexahydrate + sparfloxacin (110871-86-8) → La(NO3)(sparfloxacin(1-))2(H2O)*H2O

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	87%

formaldehyd (50-00-0) + isoxazolo[3,4-b]quinolin-3(1H)-one + sparfloxacin (110871-86-8) → 4'-(5-amino-3-carboxy-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-4-carboxy-2',6'-dimethyl-1H-spiro[[1,2,4]triazolo[4,3-a]quinoline-2,1'-piperazin]-1'-ium chloride

Conditions	Yield
Stage #1: formaldehyd; isoxazolo[3,4-b]quinolin-3(1H)-one; sparfloxacin With triethylamine In methanol at 20℃; Mannich Aminomethylation; Stage #2: With hydrogenchloride In methanol	86%

chromium chloride hexahydrate + sparfloxacin (110871-86-8) + rac-Ala-OH (302-72-7) → CrCl(sparfloxacin(1-))(DL-alanine)(H2O)*H2O

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand and DL-alanine, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	85%

chromium chloride hexahydrate + sparfloxacin (110871-86-8) → CrCl(sparfloxacin(1-))2(H2O)*H2O

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	85%

cobalt(II) chloride hexahydrate + sparfloxacin (110871-86-8) → Co(sparfloxacin(1-))2(H2O)2

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	85%

cadmium(II) chloride monohydrate + sparfloxacin (110871-86-8) → [Cd(5-amino-1-cyclopropyl-7-(cis-3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinocarboxylate)2(H2O)]Cl2

Conditions	Yield
In methanol sparfloxacin dissolved in MeOH; soln. of Cd salt in MeOH added with stirring; refluxed at 80°C (water bath) for 4 h; vol. reduced by evapn.; filtered; ppt. washed with H2O and MeOH; dried under reduced pressure at room temp.; elem. anal.;	83.9%

2-chloro-N-(5-hexyl-[1,3,4]thiadiazol-2-yl)-acetamide (15777-51-2) + sparfloxacin (110871-86-8) → [5-amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid]-5-hexylthiadiazole

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃; for 6h;	82.6%

di(pyridin-2-yl)amine (1202-34-2) + sparfloxacin (110871-86-8) + zinc(II) chloride (7646-85-7) → bis(5-amino-1-cyclopropyl-7-((3R,5S)-3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylato)(2,2'-bipyridylamine)zinc

Conditions	Yield
With potassium hydroxide In methanol soln. of sparfloxacin and KOH in MeOH added to soln. of ZnCl2 and bis(2-pyridyl)amine in MeOH; soln. allowed to evap. slowly for a few days; elem. anal.;	82%

methanol (67-56-1) + water (7732-18-5) + sparfloxacin (110871-86-8) + copper(II) perchlorate → [copper(II)(sparfloxacin)2(perchlorato)](perchlorate)*2CH3OH*3.75H2O

Conditions	Yield
In neat (no solvent) for 0.5h;	81%

sparfloxacin (110871-86-8) + rac-Ala-OH (302-72-7) + manganese(ll) chloride → Mn(sparfloxacin(1-))(DL-alanine)(H2O)2

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand and DL-alanine, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	78%

4-chloro-6-[1-(vinylsulfonyl)pyrrolidin-2-yl]benzene-1,3-diol + sparfloxacin (110871-86-8) → 5-amino-7-[(3R,5S)-4-(2-{[2-(5-chloro-2,4-dihydroxyphenyl)pyrrolidin-1-yl]sulfonyl}ethyl)-3,5-dimethylpiperazin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions	Yield
With triethylamine In ethanol; water for 15h; Michael Addition; Reflux;	77%

bis(acetylacetonato)dioxidomolybdenum(VI) + sparfloxacin (110871-86-8) → 5-amino-1-cyclopropyl-7-(cis-3,5-dimethylpiperazino)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Conditions	Yield
With potassium hydroxide In methanol a MeOH soln. of 2 equiv. of F-compd. deprotonated with 2 equiv. of KOH was added to the Mo-compd. soln. in MeOH, reflux for 2.5 h; soln. was filtered and left to slowly evaporate for a few days, crystalswere filtered off, washed with MeOH and dried, elem. anal.;	75%

nickel(II) chloride hexahydrate + sparfloxacin (110871-86-8) → Ni(sparfloxacin(1-))2(H2O)2

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	75%

copper(II) choride dihydrate + sparfloxacin (110871-86-8) → Cu(sparfloxacin(1-))2*2H2O

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	75%

cobalt(II) chloride hexahydrate + sparfloxacin (110871-86-8) + rac-Ala-OH (302-72-7) → Co(sparfloxacin(1-))(DL-alanine)(H2O)2

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand and DL-alanine, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	75%

cobalt(II) chloride hexahydrate + sparfloxacin (110871-86-8) → [Co(5-amino-1-cyclopropyl-7-(cis-3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinocarboxylate)2(H2O)]Cl2

Conditions	Yield
In methanol sparfloxacin dissolved in MeOH; soln. of Co salt in MeOH added with stirring; refluxed at 80°C (water bath) for 4 h; vol. reduced by evapn.; filtered; ppt. washed with H2O and MeOH; dried under reduced pressure at room temp.; elem. anal.;	74.8%

sparfloxacin (110871-86-8) + 2-(chloroacetamido)-5-n-butyl-1,3,4-thiadiazole (15777-44-3) → [5-amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid]-5-butyl thiadiazole

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃; for 6h;	74.6%

C12H12ClN3O3S + sparfloxacin (110871-86-8) → [5-amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid]-5-(3,4-dimethoxyphenyl)thiadiazole

Conditions	Yield
With pyridine In benzene for 48h; Reflux;	74.6%

water (7732-18-5) + sparfloxacin (110871-86-8) + zinc(II) chloride (7646-85-7) → [Zn(5-amino-1-cyclopropyl-7-(cis-3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinocarboxylate)2(H2O)]Cl2

Conditions	Yield
In methanol sparfloxacin dissolved in MeOH; soln. of Zn salt in MeOH added with stirring; refluxed at 80°C (water bath) for 4 h; vol. reduced by evapn.; filtered; ppt. washed with H2O and MeOH; dried under reduced pressure at room temp.; elem. anal.;	74%

sparfloxacin (110871-86-8) + benzoyl chloride (98-88-4) → 5-amino-7-((3S,5R)-4-benzoyl-3,5-dimethylpiperazine-1-yl)-1-cyclopropyl-6,8-difluro-4-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acid

Conditions	Yield
In methanol Reflux;	73%

iron(III) chloride hexahydrate + sparfloxacin (110871-86-8) → FeCl(sparfloxacin(1-))2(H2O)*H2O

Conditions	Yield
In ethanol; water hot H2O-EtOH soln. of metal salt added to hot EtOH soln. of ligand, stirred under reflux for 2 h, cooled; filtered, washed with EtOH, Et2O, dried in vac. desiccator over CaCl2; elem. anal.;	72%

sparfloxacin (110871-86-8) + tricyclohexyltin(IV) chloride (3091-32-5) → C37H54F2N4O3Sn

Conditions	Yield
Stage #1: sparfloxacin With methanol; sodium Reflux; Stage #2: tricyclohexyltin(IV) chloride Reflux;	72%

pyridine (110-86-1) + nickel(II) chloride hexahydrate + sparfloxacin (110871-86-8) → bis(pyridine)bis(sparfloxacinato)nickel(II)

Conditions	Yield
With KOH In methanol KOH added to MeOH soln. of sparfloxacin; added to MeOH soln. of NiCl2; pyridine added; crystd. by slow evapn. after few d; elem. anal.;	70%

hydrogen bromide (10035-10-6, 12258-64-9) + sparfloxacin (110871-86-8) + copper(ll) bromide (7789-45-9) → sparfloxacindium tetrabromidocuprate(II) monohydrate

Conditions	Yield
Heating;	70%

Upstream product

• 110872-04-3 ethyl 5-(benzylamino)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate 
• 103772-13-0 ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 107564-02-3 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester 
• 103772-14-1 5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 21655-48-1 cis-2,6-dimethylpiperazine 

Downstream Products

• 113617-63-3 1-cyclopropyl-5,6,8-trifluoro-7-(cis-3,5-dimethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 

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