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112984-60-8

112984-60-8

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  • High quality 6-Fluoro-1-Methyl-4-Oxo-7-(1-Piperazinyl)-4H-(1,3)-Thiazeto(3,2-A)Quinoline-3-Carboxylic Acid supplier in China

    Cas No: 112984-60-8

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  • 6-Fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]-thiazeto[3,2-a]-3-quinolinecarboxylic acid

    Cas No: 112984-60-8

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112984-60-8 Usage

Chemical Properties

Yellow Solid

Uses

Different sources of media describe the Uses of 112984-60-8 differently. You can refer to the following data:
1. A metabolite of Prulifloxacin (P838885). Ulifloxacin is a new quinolone antibiotic and it is effective against pneumonia.
2. A labelled metabolite of Prulifloxacin (P838885). Ulifloxacin is a new quinolone antibiotic and it is effective against pneumonia.

Check Digit Verification of cas no

The CAS Registry Mumber 112984-60-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,2,9,8 and 4 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 112984-60:
(8*1)+(7*1)+(6*2)+(5*9)+(4*8)+(3*4)+(2*6)+(1*0)=128
128 % 10 = 8
So 112984-60-8 is a valid CAS Registry Number.
InChI:InChI=1/C16H16FN3O3S/c1-8-20-11-7-12(19-4-2-18-3-5-19)10(17)6-9(11)14(21)13(16(22)23)15(20)24-8/h6-8,18H,2-5H2,1H3,(H,22,23)

112984-60-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names Ulifloxacin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:112984-60-8 SDS

112984-60-8Synthetic route

ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate
113028-17-4

ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
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 6,7-difluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate
113046-72-3

ethyl 6,7-difluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
With potassium hydroxide at 20℃; for 5h;90%
Multi-step reaction with 2 steps
1: 84 percent / dimethylformamide / Ambient temperature
2: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
Multi-step reaction with 2 steps
1: dimethyl sulfoxide / 4 h / 60 °C
2: potassium hydroxide / 5 h / 20 °C
View Scheme
3,4-difluorophenyl isothiocyanate
113028-75-4

3,4-difluorophenyl isothiocyanate

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 5 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
5: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
Multi-step reaction with 7 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
7: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
ethyl 7,6-difluoro-4-hydroxy-2-mercaptoquinoline-3-carboxylate
84339-06-0

ethyl 7,6-difluoro-4-hydroxy-2-mercaptoquinoline-3-carboxylate

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C
2: 84 percent / dimethylformamide / Ambient temperature
3: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
3,4-difluorophenyl dithiocarbamic acid triethylammonium
144514-15-8

3,4-difluorophenyl dithiocarbamic acid triethylammonium

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 6 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
6: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
Multi-step reaction with 8 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
8: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
ethyl 6,7-difluoro-4-hydroxy-2-<(methoxymethyl)thio>-quinoline-3-carboxylate
113028-77-6

ethyl 6,7-difluoro-4-hydroxy-2-<(methoxymethyl)thio>-quinoline-3-carboxylate

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 4 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
4: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
3-(3,4-difluorophenyl)-4-methyl<1,3>thiazetidin-2-ylidenemalonate
144514-35-2

3-(3,4-difluorophenyl)-4-methyl<1,3>thiazetidin-2-ylidenemalonate

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 0.350 g / PPE / 1.5 h / 80 °C
2: 84 percent / dimethylformamide / Ambient temperature
3: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
diethyl<<(3,4-difluorophenyl)amino><(methoxymethyl)-thio>methylene>malonate
113028-76-5

diethyl<<(3,4-difluorophenyl)amino><(methoxymethyl)-thio>methylene>malonate

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 5 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
5: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
[[(3,4-difluorophenyl)amino]-mercaptomethylene]-malonic acid diethyl ester potassium salt

[[(3,4-difluorophenyl)amino]-mercaptomethylene]-malonic acid diethyl ester potassium salt

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 4 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
4: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
Multi-step reaction with 6 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
6: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
3,4-difluoroaniline
3863-11-4

3,4-difluoroaniline

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 7 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
7: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
Multi-step reaction with 9 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
9: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
View Scheme
6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate-O3,O4(bis(acetato-)O)-borone
1028087-98-0

6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate-O3,O4(bis(acetato-)O)-borone

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
Stage #1: 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate-O3,O4(bis(acetato-)O)-borone With potassium hydroxide; water at 25 - 65℃; for 4h;
Stage #2: With hydrogenchloride In water at 25 - 30℃; for 1h; pH=7 - 7.5; Product distribution / selectivity;
ethyl 5,6-difluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinoline carboxylate

ethyl 5,6-difluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinoline carboxylate

ulifloxacin
112984-60-8

ulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N,N-dimethyl-formamide / 9.17 h / 10 - 55 °C
2.1: potassium hydroxide; water / 1 h / 80 - 85 °C
2.2: 1 h / 20 °C / pH 6.5 - 7
View Scheme
4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one
80715-22-6

4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one

ulifloxacin
112984-60-8

ulifloxacin

prulifloxacin
123447-62-1

prulifloxacin

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 0℃; for 5h; Large scale;95.4%
With potassium hydrogencarbonate In N,N-dimethyl-formamide for 5h; Ambient temperature;62%
Stage #1: ulifloxacin With potassium hydrogencarbonate In acetonitrile at 25 - 30℃;
Stage #2: 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one at 15 - 30℃; for 27 - 28.25h;
Stage #1: 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one; ulifloxacin With potassium hydrogencarbonate In N,N-dimethyl-formamide at 0 - 28℃; for 3 - 4h;
Stage #2: With hydrogenchloride In chloroform; water for 0.25h; pH=0.8 - 1.0;
Stage #1: ulifloxacin With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.166667h;
Stage #2: 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one In acetonitrile at 10 - 30℃; for 21h; Product distribution / selectivity;
BOC-glycine
4530-20-5

BOC-glycine

ulifloxacin
112984-60-8

ulifloxacin

7-(4-((tert-butoxycarbonyl)glycyl)piperazin-1-yl)-6-fluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

7-(4-((tert-butoxycarbonyl)glycyl)piperazin-1-yl)-6-fluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: BOC-glycine With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 4h;
Stage #2: ulifloxacin With triethylamine at 0 - 20℃;		65%
ulifloxacin
112984-60-8

ulifloxacin

descarboxymoxifloxacin
1322062-62-3

descarboxymoxifloxacin

Conditions
ConditionsYield
With sulfuric acid; water at 100℃; for 144h;40%
bromo-acetic acid 1-chloromethyl-2-(2-methyl-5-nitro-imidazol-1-yl)ethyl ester

bromo-acetic acid 1-chloromethyl-2-(2-methyl-5-nitro-imidazol-1-yl)ethyl ester

ulifloxacin
112984-60-8

ulifloxacin

7-{4-[1-chloromethyl-2-(2-methyl-5-nitroimidazol-1-yl)ethoxycarbonylmethyl]piperazin-1-yl}-6-fluoro-1-methyl-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid

7-{4-[1-chloromethyl-2-(2-methyl-5-nitroimidazol-1-yl)ethoxycarbonylmethyl]piperazin-1-yl}-6-fluoro-1-methyl-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;35%
ulifloxacin
112984-60-8

ulifloxacin

(±)-2-methyl-5-nitro-1-(oxiran-2-ylmethyl)-1H-imidazole
16773-52-7

(±)-2-methyl-5-nitro-1-(oxiran-2-ylmethyl)-1H-imidazole

6-fluoro-7-{4-[2-hydroxy-3-(2-methyl-5-nitro-imidazol-1-yl)propyl]piperazin-1-yl}-1-methyl-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid

6-fluoro-7-{4-[2-hydroxy-3-(2-methyl-5-nitro-imidazol-1-yl)propyl]piperazin-1-yl}-1-methyl-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In water; acetone at 50℃; for 20h;30%
2-Picolinic acid
98-98-6

2-Picolinic acid

ulifloxacin
112984-60-8

ulifloxacin

6-fluoro-1-methyl-4-oxo-7-(4-picolinoylpiperazin-1-yl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

6-fluoro-1-methyl-4-oxo-7-(4-picolinoylpiperazin-1-yl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 2-Picolinic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: ulifloxacin With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;		28%
4-chloromethyl-5-methyl-1,3-dioxol-2-one
80841-78-7

4-chloromethyl-5-methyl-1,3-dioxol-2-one

ulifloxacin
112984-60-8

ulifloxacin

6-fluoro-1-methyl-4-oxo-7-<4-<(2-oxo-1-methylenepropyl)oxycarbonyl>-1-piperazinyl>-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid
156834-57-0

6-fluoro-1-methyl-4-oxo-7-<4-<(2-oxo-1-methylenepropyl)oxycarbonyl>-1-piperazinyl>-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide for 22h; Ambient temperature;25%
4-bromo-1-(2-methyl-5-nitro-imidazol-1-yl)butan-2-ol

4-bromo-1-(2-methyl-5-nitro-imidazol-1-yl)butan-2-ol

ulifloxacin
112984-60-8

ulifloxacin

6-fluoro-7-{4-[3-hydroxy-4-(2-methyl-5-nitro-imidazol-1-yl)butyl]piperazin-1-yl}-1-methyl-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid

6-fluoro-7-{4-[3-hydroxy-4-(2-methyl-5-nitro-imidazol-1-yl)butyl]piperazin-1-yl}-1-methyl-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;20%
6-bromo-1-(2-methyl-5-nitro-imidazol-1-yl)hexan-2-ol

6-bromo-1-(2-methyl-5-nitro-imidazol-1-yl)hexan-2-ol

ulifloxacin
112984-60-8

ulifloxacin

6-fluoro-7-{4-[5-hydroxy-6-(2-methyl-5-nitro-imidazol-1-yl)hexyl]-piperazin-1-yl}-1-methyl-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid

6-fluoro-7-{4-[5-hydroxy-6-(2-methyl-5-nitro-imidazol-1-yl)hexyl]-piperazin-1-yl}-1-methyl-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;20%
toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester
30575-42-9

toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester

ulifloxacin
112984-60-8

ulifloxacin

6-fluoro-1-methyl-7-{4-[2-(2-methyl-5-nitro-imidazol-1-yl)ethyl]piperazin-1-yl}-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid

6-fluoro-1-methyl-7-{4-[2-(2-methyl-5-nitro-imidazol-1-yl)ethyl]piperazin-1-yl}-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 16h;20%
With tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide at 90℃; for 20h; Inert atmosphere;8%
Chloromethyl pivalate
18997-19-8

Chloromethyl pivalate

ulifloxacin
112984-60-8

ulifloxacin

(pivaloyloxy)methyl 6-fluoro-1-methyl-7-(piperazinyl)-4-oxo-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylate

(pivaloyloxy)methyl 6-fluoro-1-methyl-7-(piperazinyl)-4-oxo-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60 - 80℃; for 3h;18%
2-(bromomethyl)-6-nitro-1H-benzo[d]imidazole

2-(bromomethyl)-6-nitro-1H-benzo[d]imidazole

ulifloxacin
112984-60-8

ulifloxacin

6-fluoro-1-methyl-7-(4-((6-nitro-1H-benzo[d]imidazol-2-yl)methyl)piperazin-1-yl)4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

6-fluoro-1-methyl-7-(4-((6-nitro-1H-benzo[d]imidazol-2-yl)methyl)piperazin-1-yl)4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 18h;13%
2-(bromomethyl)-5,6-dichloro-1H-benzo[d]imidazole

2-(bromomethyl)-5,6-dichloro-1H-benzo[d]imidazole

ulifloxacin
112984-60-8

ulifloxacin

7-(4-((5,6-dichloro-1H-benzo[d]imidazol-2-yl)methyl)piperazin-1-yl)-6-fluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

7-(4-((5,6-dichloro-1H-benzo[d]imidazol-2-yl)methyl)piperazin-1-yl)-6-fluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 18h;10%
4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one
80715-22-6

4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one

ulifloxacin
112984-60-8

ulifloxacin

A

prulifloxacin
123447-62-1

prulifloxacin

B

6-fluoro-1-methyl-4-oxo-7-<4-<(2-oxo-1-methylenepropyl)oxycarbonyl>-1-piperazinyl>-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid
156834-57-0

6-fluoro-1-methyl-4-oxo-7-<4-<(2-oxo-1-methylenepropyl)oxycarbonyl>-1-piperazinyl>-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid

C

7-<4-<1-<4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinolin-7-yl)>-1-piperazinylmethyl>-2-oxopropoxycarbonyl>-1-piperazinyl>-6-fluoro-1-methyl-4-oxo-4H-<1,3>thazeto<3,2-a>quinoline-3-carboxylic acid

7-<4-<1-<4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinolin-7-yl)>-1-piperazinylmethyl>-2-oxopropoxycarbonyl>-1-piperazinyl>-6-fluoro-1-methyl-4-oxo-4H-<1,3>thazeto<3,2-a>quinoline-3-carboxylic acid

D

1,1-bis<(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl>-4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinoline-7-yl)-1-piperazinium bromide

1,1-bis<(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl>-4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinoline-7-yl)-1-piperazinium bromide

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 30℃; for 2h; Product distribution; Rate constant; various periods of time (3 h); activation energy 29.1 kJ mol-1;A 93.6 % Spectr.
B 2.0 % Spectr.
C 0.5 % Spectr.
D 1.1 % Spectr.
4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one
80715-22-6

4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one

ulifloxacin
112984-60-8

ulifloxacin

A

6-fluoro-1-methyl-4-oxo-7-<4-<(2-oxo-1-methylenepropyl)oxycarbonyl>-1-piperazinyl>-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid
156834-57-0

6-fluoro-1-methyl-4-oxo-7-<4-<(2-oxo-1-methylenepropyl)oxycarbonyl>-1-piperazinyl>-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid

B

7-<4-<1-<4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinolin-7-yl)>-1-piperazinylmethyl>-2-oxopropoxycarbonyl>-1-piperazinyl>-6-fluoro-1-methyl-4-oxo-4H-<1,3>thazeto<3,2-a>quinoline-3-carboxylic acid

7-<4-<1-<4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinolin-7-yl)>-1-piperazinylmethyl>-2-oxopropoxycarbonyl>-1-piperazinyl>-6-fluoro-1-methyl-4-oxo-4H-<1,3>thazeto<3,2-a>quinoline-3-carboxylic acid

C

1,1-bis<(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl>-4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinoline-7-yl)-1-piperazinium bromide

1,1-bis<(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl>-4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinoline-7-yl)-1-piperazinium bromide

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide for 24h; Ambient temperature;
ulifloxacin
112984-60-8

ulifloxacin

prulifloxacin
123447-62-1

prulifloxacin

7-<4-<1-<4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinolin-7-yl)>-1-piperazinylmethyl>-2-oxopropoxycarbonyl>-1-piperazinyl>-6-fluoro-1-methyl-4-oxo-4H-<1,3>thazeto<3,2-a>quinoline-3-carboxylic acid

7-<4-<1-<4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinolin-7-yl)>-1-piperazinylmethyl>-2-oxopropoxycarbonyl>-1-piperazinyl>-6-fluoro-1-methyl-4-oxo-4H-<1,3>thazeto<3,2-a>quinoline-3-carboxylic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 30.9℃; Rate constant;
ulifloxacin
112984-60-8

ulifloxacin

6-fluoro-1-methyl-4-oxo-7-<4-<(2-oxo-1-methylenepropyl)oxycarbonyl>-1-piperazinyl>-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid
156834-57-0

6-fluoro-1-methyl-4-oxo-7-<4-<(2-oxo-1-methylenepropyl)oxycarbonyl>-1-piperazinyl>-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid

7-<4-<1-<4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinolin-7-yl)>-1-piperazinylmethyl>-2-oxopropoxycarbonyl>-1-piperazinyl>-6-fluoro-1-methyl-4-oxo-4H-<1,3>thazeto<3,2-a>quinoline-3-carboxylic acid

7-<4-<1-<4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinolin-7-yl)>-1-piperazinylmethyl>-2-oxopropoxycarbonyl>-1-piperazinyl>-6-fluoro-1-methyl-4-oxo-4H-<1,3>thazeto<3,2-a>quinoline-3-carboxylic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 30.9℃; Rate constant;
4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one
80715-22-6

4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one

ulifloxacin
112984-60-8

ulifloxacin

A

prulifloxacin
123447-62-1

prulifloxacin

B

6-Fluoro-1-methyl-7-[4-(5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl)-piperazin-1-yl]-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester

6-Fluoro-1-methyl-7-[4-(5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl)-piperazin-1-yl]-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester

Conditions
ConditionsYield
With potassium hydrogencarbonate for 3h; Product distribution; also in presence of DIPEA, car. concn. of substrates;
4-chloromethyl-5-methyl-1,3-dioxol-2-one
80841-78-7

4-chloromethyl-5-methyl-1,3-dioxol-2-one

ulifloxacin
112984-60-8

ulifloxacin

prulifloxacin
123447-62-1

prulifloxacin

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; sodium bromide 1.) DMF, 303 K, 2 h, 2.) DMF, 304 K, 1 h; Yield given. Multistep reaction;

112984-60-8Relevant articles and documents

Ulifloxacin hydrochloride crystal as well as preparation method and application thereof

-

Paragraph 0057; 0058, (2018/03/24)

The invention provides an ulifloxacin hydrochloride crystal. The crystal uses an X-ray powder diffraction pattern of Cu-Ka radiation and has following peaks denoted with 2theta angles: 8.859 degrees plus or minus 0.2 degrees, 15.233 degrees plus or minus 0.2 degrees, 15.284 degrees plus or minus 0.2 degrees, 22.153 degrees plus or minus 0.2 degrees, 25.217 degrees plus or minus 0.2 degrees and 26.750 degrees plus or minus 0.2 degrees. The invention also provides a preparation method of the crystal, medicine composition containing the crystal as well as a pharmaceutical application of the crystal and the medicine composition. The provided crystal has good reproducibility, the preparation method is simple, and dosage of an organic solvent is reduced. Experiments prove that the novel crystal and an original ulifloxacin hydrochloride crystal both have a remarkable effect in the aspects of solubility, stability, moisture absorption and in-vivo therapy effect, and the novel crystal can be prepared in multiple dosage forms and has good clinical application potential.

A method for preparing of plurichari (by machine translation)

-

Paragraph 0024; 0037; 0038; 0039, (2016/10/07)

The invention relates to a prepration method of a compound prulifloxacin as shown in the formula (I), wherein the chemical name of prulifloxacin is 6-floro-1-methyl-7-[4-(5-methyl-2-oxo1,3-dioxo hetercyclopentene-4-yl)methyl-1-piperazinyl-4-oxo-4H-[1,3] thiaazacyclobutane[3,2-a] quinoline-3-carboxylic acid. The preparation method provided by the invention is a preparation method of prulifloxacin suitable for industrialized production, simple in process, high in purity and high in yield.

PROCESS FOR THE PREPARATION OF HIGHLY PURE PRULIFLOXACIN

-

Page/Page column 15, (2009/09/05)

The present invention provides an industrially advantageous process for the preparation of highly pure prulifloxacin of formula I and its pharmaceutically acceptable salts. The present i innvention a also provides a novel process for the purification of prulifloxacin acid addition salt.

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