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112811-72-0

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  • High quality 1-Cyclopropyl-6,7-Difluoro-1,4-Dihydro-8-Methoxy-4-Oxo-3-Quinoline Carboxylic Acid supplier in China

    Cas No: 112811-72-0

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  • High Quality 99% 112811-72-0 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid Manufacturer

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112811-72-0 Usage

Chemical Properties

Off-White to Light-Yellow Powder

Uses

Different sources of media describe the Uses of 112811-72-0 differently. You can refer to the following data:
1. Moxifloxacin intermediate
2. Moxifloxacin intermediate.

Check Digit Verification of cas no

The CAS Registry Mumber 112811-72-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,2,8,1 and 1 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 112811-72:
(8*1)+(7*1)+(6*2)+(5*8)+(4*1)+(3*1)+(2*7)+(1*2)=90
90 % 10 = 0
So 112811-72-0 is a valid CAS Registry Number.
InChI:InChI=1/C14H11F2NO4/c1-21-13-10(16)9(15)4-7-11(13)17(6-2-3-6)5-8(12(7)18)14(19)20/h4-6H,2-3H2,1H3,(H,19,20)

112811-72-0SDS

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 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1.2 Other means of identification

Product number -
Other names 1-Cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

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:112811-72-0 SDS

112811-72-0Synthetic route

ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate
112811-71-9

ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 65℃; for 15h; Solvent; Temperature;96.83%
With sulfuric acid; acetic acid In water for 2h; Reflux;95.92%
With hydrogenchloride for 3h; Heating;90%
1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxo-3-quinoline carboxylic acid
154093-72-8

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxo-3-quinoline carboxylic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

A

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid methyl ester
141290-02-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid methyl ester

B

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
With potassium chloride In acetone Product distribution / selectivity; Heating / reflux;
1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid methyl ester
141290-02-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid methyl ester

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
With water; potassium carbonate for 0.5h; Product distribution / selectivity; Heating / reflux;
ethyl 3-(cyclopropylamino)-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate
112811-70-8

ethyl 3-(cyclopropylamino)-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
With sodium fluoride In N,N-dimethyl-formamide
Multi-step reaction with 2 steps
1: sodiumfluoride / N,N-dimethyl-formamide / 5 h
2: sulfuric acid; water / acetic acid / 1 h
View Scheme
2,4,5-trifluoro-3-methoxy-benzamide
112811-64-0

2,4,5-trifluoro-3-methoxy-benzamide

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: sulfuric acid / 3.5 h / 100 °C
2: thionyl chloride / 3 h
3: magnesium ethylate / toluene
4: toluene-4-sulfonic acid / water / 9 h
5: acetic anhydride / 11 h
6: ethanol / 2 h / 20 °C
7: sodiumfluoride / N,N-dimethyl-formamide / 5 h
8: sulfuric acid; water / acetic acid / 1 h
View Scheme
3-methoxy-2,4,5-trifluorobenzonitrile
112811-63-9

3-methoxy-2,4,5-trifluorobenzonitrile

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: sulfuric acid; water / 1 h / 110 °C
2: sulfuric acid / 3.5 h / 100 °C
3: thionyl chloride / 3 h
4: magnesium ethylate / toluene
5: toluene-4-sulfonic acid / water / 9 h
6: acetic anhydride / 11 h
7: ethanol / 2 h / 20 °C
8: sodiumfluoride / N,N-dimethyl-formamide / 5 h
9: sulfuric acid; water / acetic acid / 1 h
View Scheme
diethyl 3-methoxy-2,4,5-trifluorobenzoylmalonate
112811-67-3

diethyl 3-methoxy-2,4,5-trifluorobenzoylmalonate

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: toluene-4-sulfonic acid / water / 9 h
2: acetic anhydride / 11 h
3: ethanol / 2 h / 20 °C
4: sodiumfluoride / N,N-dimethyl-formamide / 5 h
5: sulfuric acid; water / acetic acid / 1 h
View Scheme
1-bromo-2,4,5-trifluoro-3-methoxybenzene
13332-24-6

1-bromo-2,4,5-trifluoro-3-methoxybenzene

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1-methyl-pyrrolidin-2-one / 4.5 h / 140 - 150 °C
2: sulfuric acid; water / 1 h / 110 °C
3: sulfuric acid / 3.5 h / 100 °C
4: thionyl chloride / 3 h
5: magnesium ethylate / toluene
6: toluene-4-sulfonic acid / water / 9 h
7: acetic anhydride / 11 h
8: ethanol / 2 h / 20 °C
9: sodiumfluoride / N,N-dimethyl-formamide / 5 h
10: sulfuric acid; water / acetic acid / 1 h
View Scheme
3-methoxy-2,4,5-trifluorobenzoic acid
112811-65-1

3-methoxy-2,4,5-trifluorobenzoic acid

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: thionyl chloride / 3 h
2: magnesium ethylate / toluene
3: toluene-4-sulfonic acid / water / 9 h
4: acetic anhydride / 11 h
5: ethanol / 2 h / 20 °C
6: sodiumfluoride / N,N-dimethyl-formamide / 5 h
7: sulfuric acid; water / acetic acid / 1 h
View Scheme
2,4,5-trifluoro-3-methoxybenzoyl chloride
112811-66-2

2,4,5-trifluoro-3-methoxybenzoyl chloride

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: magnesium ethylate / toluene
2: toluene-4-sulfonic acid / water / 9 h
3: acetic anhydride / 11 h
4: ethanol / 2 h / 20 °C
5: sodiumfluoride / N,N-dimethyl-formamide / 5 h
6: sulfuric acid; water / acetic acid / 1 h
View Scheme
ethyl 3-methoxy-2,4,5-trifluorobenzoylacetate
112811-68-4

ethyl 3-methoxy-2,4,5-trifluorobenzoylacetate

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic anhydride / 11 h
2: ethanol / 2 h / 20 °C
3: sodiumfluoride / N,N-dimethyl-formamide / 5 h
4: sulfuric acid; water / acetic acid / 1 h
View Scheme
ethyl 3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate
122375-85-3

ethyl 3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol / 2 h / 20 °C
2: sodiumfluoride / N,N-dimethyl-formamide / 5 h
3: sulfuric acid; water / acetic acid / 1 h
View Scheme
1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6,7-difluoro-3-(imidazole-1-carbonyl)-8-methoxy-1H-quinolin-4-one
869310-07-6

1-cyclopropyl-6,7-difluoro-3-(imidazole-1-carbonyl)-8-methoxy-1H-quinolin-4-one

Conditions
ConditionsYield
In tetrahydrofuran Heating / reflux;100%
In chloroform Heating / reflux;100%
In tetrahydrofuran Heating / reflux;100%
In tetrahydrofuran Heating / reflux;100%
boric acid
11113-50-1

boric acid

acetic anhydride
108-24-7

acetic anhydride

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid-O3,O4(bis(acyloxy-O)) borate
139693-52-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid-O3,O4(bis(acyloxy-O)) borate

Conditions
ConditionsYield
Stage #1: boric acid; acetic anhydride With potassium hydroxide; zinc(II) chloride at 100℃; for 12h;
Stage #2: 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid at 50℃; for 1h; Concentration; Temperature; Reagent/catalyst;
97.4%
1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-1,4-dihydro-6,7-difluoro-8-methoxy-4-oxo-quinoline-3-carboxylic acid difluoroborate ester
847233-56-1

1-cyclopropyl-1,4-dihydro-6,7-difluoro-8-methoxy-4-oxo-quinoline-3-carboxylic acid difluoroborate ester

Conditions
ConditionsYield
Stage #1: 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid With potassium carbonate In tetrahydrofuran at 20℃; for 0.0833333h;
Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran at 20 - 66℃; for 6.08333h;
97%
With boron trifluoride diethyl etherate; potassium carbonate In tetrahydrofuran at 20 - 66℃; Inert atmosphere;97%
With BF3OEt In various solvent(s) Cyclization; Heating;83%
With boron trifluoride diethyl etherate In tetrahydrofuran for 36h; Heating / reflux;
Multi-step reaction with 2 steps
1: acetonitrile / 1 h / 70 - 80 °C / Inert atmosphere; Large scale
2: 1 h / 0 - 15 °C / Large scale
View Scheme
boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

(1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-(oxo-κO)-3-quinoline-carboxylato-κO3)difluoro-Boron

(1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-(oxo-κO)-3-quinoline-carboxylato-κO3)difluoro-Boron

Conditions
ConditionsYield
Stage #1: 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid With potassium carbonate In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: boron trifluoride diethyl etherate In tetrahydrofuran at 60℃; for 6h; Temperature; Reagent/catalyst;
97%
2-Amino-2-methyl-1-propanol
124-68-5

2-Amino-2-methyl-1-propanol

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

C18H18F2N2O3

C18H18F2N2O3

Conditions
ConditionsYield
In toluene at 105 - 115℃; Temperature; Solvent; Inert atmosphere; Industrial scale;96.6%
1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

(1S,6S)-2,8-diazabicyclo[4.3.0]nonane
151213-40-0

(1S,6S)-2,8-diazabicyclo[4.3.0]nonane

moxifloxacin
151096-09-2

moxifloxacin

Conditions
ConditionsYield
With [BCl2(4-picoline)][AlCl4]; triethylamine In methanol at 85℃; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;96%
In dimethyl sulfoxide at 65 - 70℃; for 6 - 8h;89.7%
With triethylamine In N,N-dimethyl-formamide; acetonitrile at 0 - 78℃; for 11h; Reflux;66%
[R,R]-2,8-diazabicyclo[4.3.0]nonane
151213-42-2

[R,R]-2,8-diazabicyclo[4.3.0]nonane

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

moxifloxacin

moxifloxacin

Conditions
ConditionsYield
With nano iron oxide on ZrO2 coated sulfonic acid In water for 0.416667h; Reflux;96%
at 150℃; Microwave irradiation;83%
triacetoxyborane
4887-24-5

triacetoxyborane

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid-(O3,O4)-bis-(acetate-O)borate

1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid-(O3,O4)-bis-(acetate-O)borate

Conditions
ConditionsYield
In water at 0 - 90℃; for 4h;95.3%
3-methylaminopiperidine dihydrochloride

3-methylaminopiperidine dihydrochloride

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-(3-methylaminopiperidin-1-yl)-3-quinolinecarboxylic acid

1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-(3-methylaminopiperidin-1-yl)-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Stage #1: 3-methylaminopiperidine dihydrochloride; 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid With boron trifluoride-tetrahydrofuran complex; triethylamine In acetonitrile at 20℃; for 26h;
Stage #2: With methanol for 6h; Reflux;
Stage #3: With sodium hydroxide In methanol; water at 20℃; for 16h; pH=8;
92%
With triethylamine In acetonitrile
(+/-)-2-methylpiperazine bis(hydrochloride)
13264-88-5, 66918-24-9, 75336-85-5, 75336-89-9, 93334-99-7

(+/-)-2-methylpiperazine bis(hydrochloride)

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Stage #1: (+/-)-2-methylpiperazine bis(hydrochloride); 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid With boron trifluoride-tetrahydrofuran complex; triethylamine In acetonitrile at 20℃; for 25h;
Stage #2: With methanol for 5h; Reflux;
Stage #3: With sodium hydroxide In methanol; water at 20℃; for 16h; pH=7;
91%
L-Tartaric acid
87-69-4

L-Tartaric acid

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

(1S,6S)-2,8-diazabicyclo[4.3.0]nonane
151213-40-0

(1S,6S)-2,8-diazabicyclo[4.3.0]nonane

L(+)-moxifloxacin tartrate
1082245-30-4

L(+)-moxifloxacin tartrate

Conditions
ConditionsYield
Stage #1: 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid; (1S,6S)-2,8-diazabicyclo[4.3.0]nonane In N,N-dimethyl-formamide at 65 - 70℃; for 6 - 8h;
Stage #2: L-Tartaric acid In N,N-dimethyl-formamide at 25 - 80℃; for 13 - 16h; Product distribution / selectivity;
90.32%
1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxo-3-quinoline carboxylic acid
154093-72-8

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxo-3-quinoline carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; calcium chloride In water; dimethyl sulfoxide at -5 - 25℃; for 3.5h; pH=4;90%
With hydrogen bromide; acetic acid at 100℃; for 24h;
Stage #1: 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid With hydrogen bromide In acetic acid at 100℃; for 1h;
Stage #2: With water In acetic acid at 0℃;
With hydrogen bromide; acetic acid at 100℃; for 24h;
1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

(1S,6S)-2,8-diazabicyclo[4.3.0]nonane
151213-40-0

(1S,6S)-2,8-diazabicyclo[4.3.0]nonane

moxifloxacin hydrochloride
186826-86-8

moxifloxacin hydrochloride

Conditions
ConditionsYield
Stage #1: 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid; (1S,6S)-2,8-diazabicyclo[4.3.0]nonane With titanium(IV) isopropylate; triethylamine In isopropyl alcohol at 100℃; Inert atmosphere;
Stage #2: With hydrogenchloride In methanol at 20℃; for 1h; pH=1; Solvent; Reagent/catalyst;
90%
Multi-step reaction with 2 steps
1: Alkaline conditions
2: hydrogenchloride
View Scheme
Stage #1: 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid; (1S,6S)-2,8-diazabicyclo[4.3.0]nonane With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20 - 85℃; for 36h; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 15℃; for 1h; pH=1.4 - 1.8; Inert atmosphere;
3.3 g
cycloperhydroisoindole
21850-12-4

cycloperhydroisoindole

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6-fluoro-8-methoxy-7-(octahydro-2H-isoindol-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

1-cyclopropyl-6-fluoro-8-methoxy-7-(octahydro-2H-isoindol-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions
ConditionsYield
With triethylamine In acetonitrile for 24h; Reflux;89%
pyrrolidine
123-75-1

pyrrolidine

Trimethyl borate
121-43-7

Trimethyl borate

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(pyrrolidin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid

1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(pyrrolidin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid

Conditions
ConditionsYield
In ethanol; acetonitrile88.2%
diethyl amine hydrochloride
660-68-4

diethyl amine hydrochloride

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-N,N-diethyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxamide
1028205-74-4

1-cyclopropyl-N,N-diethyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 10 - 35℃; Inert atmosphere;87.3%
diphenyldisulfane
882-33-7

diphenyldisulfane

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6,7-difluoro-8-methoxy-3-(phenylthio)quinolin-4(1H)-one

1-cyclopropyl-6,7-difluoro-8-methoxy-3-(phenylthio)quinolin-4(1H)-one

Conditions
ConditionsYield
With palladium diacetate; triphenylphosphine; silver carbonate In dimethyl sulfoxide at 130℃; for 12h; Schlenk technique;87%
Trimethyl borate
121-43-7

Trimethyl borate

(RS)-3-(acetyl-methyl-amino)-pyrrolidine
79286-87-6

(RS)-3-(acetyl-methyl-amino)-pyrrolidine

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-[3-(N-acetyl-N-methylamino)pyrrolidino]pyrrolidino-3-quinolinecarboxylic acid

1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-[3-(N-acetyl-N-methylamino)pyrrolidino]pyrrolidino-3-quinolinecarboxylic acid

Conditions
ConditionsYield
In ethanol; acetonitrile83.9%
C14H18N2O2S

C14H18N2O2S

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

C28H28FN3O6S

C28H28FN3O6S

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 80℃; for 3h;82.3%
(RS)-2-methylpiperazine
109-07-9

(RS)-2-methylpiperazine

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Stage #1: 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid With 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 76 - 80℃; for 1h; Heating / reflux;
Stage #2: With boron trifluoride diethyl etherate In acetonitrile at 0 - 25℃; for 2h;
Stage #3: (RS)-2-methylpiperazine With triethylamine In acetonitrile at 15 - 25℃; for 3h; pH=~ 9;
81.8%
In dimethyl sulfoxide at 55℃; for 24h;66%
In dimethyl sulfoxide at 60 - 65℃; for 29 - 45h;53.7%
In dimethyl sulfoxide at 20 - 73℃; for 13.9167 - 14.3333h;52%
In dimethyl sulfoxide at 70 - 95℃; for 2h;
C26H26N2

C26H26N2

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

C40H36FN3O4

C40H36FN3O4

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 80℃; for 3h;81.8%
C12H20N2O2

C12H20N2O2

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

C26H30FN3O6

C26H30FN3O6

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 80℃; for 3h;81.5%
C7H9N3O2

C7H9N3O2

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

C21H19FN4O6
1018938-14-1

C21H19FN4O6

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide for 0.0333333h; microwave irradiation;79%
4,4-ethylenedioxy-piperidine
177-11-7

4,4-ethylenedioxy-piperidine

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cylopropyl-7-(1,4-dioxa-8-aza-spiro[4,5]dec-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
848070-83-7

1-cylopropyl-7-(1,4-dioxa-8-aza-spiro[4,5]dec-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide for 0.0333333h; microwave irradiation;73%
decahydroisoquinoline
2744-08-3, 2744-09-4, 6329-61-9

decahydroisoquinoline

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6-fluoro-8-methoxy-7-(octahydroisoquinolin-2(1H)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

1-cyclopropyl-6-fluoro-8-methoxy-7-(octahydroisoquinolin-2(1H)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions
ConditionsYield
With triethylamine In acetonitrile for 24h; Reflux;73%
1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

(1S,6S)-2,8-diazabicyclo[4.3.0]nonane
151213-40-0

(1S,6S)-2,8-diazabicyclo[4.3.0]nonane

1-cyclopropyl-6-fluoro-8-hydroxy-7-((4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
721970-36-1

1-cyclopropyl-6-fluoro-8-hydroxy-7-((4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid With isobutylamine; copper dichloride In methanol; ethylene glycol at 50℃; for 4h; Inert atmosphere;
Stage #2: (1S,6S)-2,8-diazabicyclo[4.3.0]nonane In methanol; ethylene glycol for 5h; Reflux;
Stage #3: With sodium hydroxide In methanol; water; ethylene glycol for 1h; Reflux;
72.1%
Thiomorpholin
123-90-0

Thiomorpholin

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-Cyclopropyl-6-fluoro-8-methoxy-7-thiomorpholino-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
114213-99-9

1-Cyclopropyl-6-fluoro-8-methoxy-7-thiomorpholino-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide for 0.0333333h; microwave irradiation;70%
N,N-diethylpiperidine-3-carboxamide
3367-95-1

N,N-diethylpiperidine-3-carboxamide

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
112811-72-0

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

C24H30FN3O5
1018937-94-4

C24H30FN3O5

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide for 0.0333333h; microwave irradiation;70%

112811-72-0Relevant articles and documents

Synthesis and crystal structure of 1-cyclopropyl-6,7-difluoro-8-methoxy-4- oxo-1,4-dihydro-3-quinoline carboxylic acid-(O3,O4)-bis-(acetate-O)borate

Li, Fei,Zhang, Jie,Jiang, Yu,Jin, Lei,Zhang, Chuan

, p. 6079 - 6082 (2013)

The crystal structure of the 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1, 4-dihydro-3-quinoline carboxylic acid-(O3,O4)-bis-(acetate-O)borate has been determined by single crystal X-ray diffraction method. The crystal belongs to monoclinic with space group P2(1)/n, with a = 16.818(9), b = 6.585(4), c = 18.663(4)?, a = 90, b = 107.351(7), g = 90, V = 1972.8(18)?3, Z = 4, Dx = 1.479 Mg/m3, l(MoKa) = 0.128, F(000) = 908, ?(MoKa) = 0.128 mm-1, R = 0.1083 and wR = 0.3062 for 2378 reflections with I > 2s(I). The two rings of fluoroquinolone and borate ring are almost coplanar with dihedral angles values lower than 2. The crystal structure is stabilized by intermolecular hydrogen bonds and p-p stacking interactions.

Compound and preparation method thereof

-

Paragraph 0067; 0068; 0069, (2018/03/24)

The invention provides a compound and a preparation method of the compound, wherein the compound has the structure as shown in the formula 1, and the compound is taken as a standard substance or a reference substance, therefore, the quality of moxifloxacin raw medicines and preparation products can be effectively controlled.

Synthesis and structure-activity relationship of 4-quinolone-3-carboxylic acid based inhibitors of glycogen synthase kinase-3β

Cociorva, Oana M.,Li, Bei,Nomanbhoy, Tyzoon,Li, Qiang,Nakamura, Ayako,Nakamura, Kai,Nomura, Masahiro,Okada, Kyoko,Seto, Shigeki,Yumoto, Kazuhiro,Liyanage, Marek,Zhang, Melissa C.,Aban, Arwin,Leen, Brandon,Szardenings, Anna Katrin,Rosenblum, Jonathan S.,Kozarich, John W.,Kohno, Yasushi,Shreder, Kevin R.

scheme or table, p. 5948 - 5951 (2011/10/18)

The synthesis, GSK-3β inhibitory activity, and anti-microbial activity of bicyclic and tricyclic derivatives of the 5,7-diamino-6-fluoro-4-quinolone- 3-carboxylic acid scaffold were studied. Kinase selectivity profiling indicated that members of this class were potent and highly selective GSK-3 inhibitors.

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