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2-Amino-6-chloro-3-nitropyridine is a chemical compound characterized by its yellow powder appearance. It is an essential raw material and intermediate utilized in various industries, including organic synthesis, pharmaceuticals, agrochemicals, and dyestuffs, due to its unique chemical properties.

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  • 27048-04-0 Structure
  • Basic information

    1. Product Name: 2-Amino-6-chloro-3-nitropyridine
    2. Synonyms: 6-CHLORO-3-NITROPYRIDIN-2-AMINE;2-AMINO-6-CHLORO-3-NITROPYRIDINE;2-AMINO-3-NITRO-6-CHLOROPYRIDINE;LABOTEST-BB LT00012599;6-chloro-3-nitropyridin-2-ylamine;2-amino-3-nitrochloropyridine;2-AMINO-6-CHLOR-3-NITROPYRIDIN 95%;2-Amino-3-nitro-6-chloropyridi
    3. CAS NO:27048-04-0
    4. Molecular Formula: C5H4ClN3O2
    5. Molecular Weight: 173.56
    6. EINECS: 248-188-5
    7. Product Categories: Amines;blocks;NitroCompounds;Pyridines;Pyridine;pyridine derivative;Aromatics;Heterocycles;Miscellaneous Reagents
    8. Mol File: 27048-04-0.mol
  • Chemical Properties

    1. Melting Point: 195-196
    2. Boiling Point: 339.9 °C at 760 mmHg
    3. Flash Point: 159.4 °C
    4. Appearance: Yellow/Crystalline
    5. Density: 1.596 g/cm3
    6. Vapor Pressure: 8.89E-05mmHg at 25°C
    7. Refractive Index: 1.657
    8. Storage Temp.: Refrigerator
    9. Solubility: Chloroform, DMSO
    10. PKA: -1.69±0.50(Predicted)
    11. Water Solubility: Slightly soluble in water. Soluble in dimethyl sulfoxide and chloroform.
    12. CAS DataBase Reference: 2-Amino-6-chloro-3-nitropyridine(CAS DataBase Reference)
    13. NIST Chemistry Reference: 2-Amino-6-chloro-3-nitropyridine(27048-04-0)
    14. EPA Substance Registry System: 2-Amino-6-chloro-3-nitropyridine(27048-04-0)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 22-26-36/37/39
    4. RIDADR: 2811
    5. WGK Germany:
    6. RTECS:
    7. HazardClass: 6.1
    8. PackingGroup:
    9. Hazardous Substances Data: 27048-04-0(Hazardous Substances Data)

27048-04-0 Usage

Uses

Used in Organic Synthesis:
2-Amino-6-chloro-3-nitropyridine is used as a key intermediate for the synthesis of various organic compounds. Its unique structure allows for further chemical reactions and modifications, making it a valuable component in the development of new molecules and materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Amino-6-chloro-3-nitropyridine is used as a building block for the development of new drugs. Its chemical properties enable it to be incorporated into the structure of potential therapeutic agents, contributing to the discovery of novel medications.
Used in Agrochemicals:
2-Amino-6-chloro-3-nitropyridine is employed as an intermediate in the production of agrochemicals, such as pesticides and herbicides. Its incorporation into these products can enhance their effectiveness in controlling pests and weeds, ultimately contributing to increased crop yields and food security.
Used in Dyestuffs:
In the dyestuffs industry, 2-Amino-6-chloro-3-nitropyridine is used as a crucial component in the synthesis of various dyes and pigments. Its unique chemical properties allow for the creation of a wide range of colors and shades, making it an indispensable part of the dye manufacturing process.

Check Digit Verification of cas no

The CAS Registry Mumber 27048-04-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,7,0,4 and 8 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 27048-04:
(7*2)+(6*7)+(5*0)+(4*4)+(3*8)+(2*0)+(1*4)=100
100 % 10 = 0
So 27048-04-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H4ClN3O2/c6-4-2-1-3(9(10)11)5(7)8-4/h1-2H,(H2,7,8)

27048-04-0 Well-known Company Product Price

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  • Alfa Aesar

  • (H64634)  2-Amino-6-chloro-3-nitropyridine, 98%   

  • 27048-04-0

  • 25g

  • 588.0CNY

  • Detail
  • Alfa Aesar

  • (H64634)  2-Amino-6-chloro-3-nitropyridine, 98%   

  • 27048-04-0

  • 100g

  • 1960.0CNY

  • Detail

27048-04-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Amino-6-chloro-3-nitropyridine

1.2 Other means of identification

Product number -
Other names 2-Amino-3-nitro-6-chloropyridi

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:27048-04-0 SDS

27048-04-0Synthetic route

2,6-dicholoro-3-nitropyridine
16013-85-7

2,6-dicholoro-3-nitropyridine

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

Conditions
ConditionsYield
With ammonia In ethanol at 0℃; for 3h;93.6%
Stage #1: 2,6-dicholoro-3-nitropyridine With ammonia In ethanol at 0℃; for 3h;
Stage #2: In ethanol at 20℃; for 16h; Sealed tube;
93.6%
With ammonia In ethanol at 0 - 20℃;92%
2,6-dicholoro-3-nitropyridine
16013-85-7

2,6-dicholoro-3-nitropyridine

A

2,6-diamino-3-nitro-pyridine
3346-63-2

2,6-diamino-3-nitro-pyridine

B

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

Conditions
ConditionsYield
With ammonia In ethanolA n/a
B 65%
2-chloro-5-nitropyridine
4548-45-2

2-chloro-5-nitropyridine

A

4,6-diamino-2-chloro-5-nitropyridine
52559-13-4

4,6-diamino-2-chloro-5-nitropyridine

B

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

Conditions
ConditionsYield
With potassium permanganate; ammonia at -33℃; for 5h;A 12%
B 57%
2-chloro-5-nitropyridine
4548-45-2

2-chloro-5-nitropyridine

A

5-nitro-pyridin-2-ylamine
4214-76-0

5-nitro-pyridin-2-ylamine

B

4-amino-2-chloro-5-nitropyridine
2604-39-9

4-amino-2-chloro-5-nitropyridine

C

5-nitro-2-pyridone
5418-51-9

5-nitro-2-pyridone

D

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

Conditions
ConditionsYield
With potassium permanganate; ammonia; potassium amideA 43%
B 6%
C 5%
D 10%
With ammonia; potassium amide at -33℃; for 1h; Product distribution; Mechanism; also in the presence of potassium permanganate; also for 2-chloro-3,5-dinitropyridine;A 40%
B n/a
C 12%
D n/a
2-chloro-5-nitropyridine
4548-45-2

2-chloro-5-nitropyridine

A

4-amino-2-chloro-5-nitropyridine
2604-39-9

4-amino-2-chloro-5-nitropyridine

B

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

Conditions
ConditionsYield
With O-Methylhydroxylamin; potassium tert-butylate; zinc(II) chloride In various solvent(s) Ambient temperature;A 13%
B 9%
2-amino-3-nitro-6-hydroxypyridine
211555-30-5

2-amino-3-nitro-6-hydroxypyridine

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

Conditions
ConditionsYield
With trichlorophosphate at 100℃;
With trichlorophosphate at 20 - 100℃;
2-chloro-6-methoxy-3-nitropyridine
38533-61-8

2-chloro-6-methoxy-3-nitropyridine

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. NH3 / 72 h
2: HBr; AcOH / 60 °C
3: POCl3 / 100 °C
View Scheme
6-methoxy-3-nitropyridin-2-amine
73896-36-3

6-methoxy-3-nitropyridin-2-amine

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HBr; AcOH / 60 °C
2: POCl3 / 100 °C
View Scheme
2,6-dichloropyridine
2402-78-0

2,6-dichloropyridine

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; nitric acid / -15 - 150 °C
2: ammonium hydroxide / 5 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: nitric acid; sulfuric acid / 100 - 105 °C
2: ammonium hydroxide / isopropyl alcohol / 72 h / 35 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium nitrate; sulfuric acid / 10.5 h / 20 - 120 °C
2: ammonia / ethanol / 0 - 20 °C
View Scheme
morpholine
110-91-8

morpholine

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

2-amino-6-(morpholin-4-yl)-3-nitropyridine
144435-16-5

2-amino-6-(morpholin-4-yl)-3-nitropyridine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;100%
at 70℃; for 5h;92%
With triethylamine In isopropyl alcohol at 110℃; for 0.25h; Microwave irradiation;86%
(R)-piperidin-3-yl(pyrrolidin-1-yl)methanone hydrochloride

(R)-piperidin-3-yl(pyrrolidin-1-yl)methanone hydrochloride

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

(R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl) (pyrrolidin-1-yl)methanone

(R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl) (pyrrolidin-1-yl)methanone

Conditions
ConditionsYield
With triethylamine In acetonitrile at 10 - 80℃; for 1h; Inert atmosphere;100%
Stage #1: (R)-piperidin-3-yl(pyrrolidin-1-yl)methanone hydrochloride With triethylamine In acetonitrile at 15 - 20℃; for 1.5h; Large scale;
Stage #2: 2-amino-6-chloro-3-nitropyridine In acetonitrile at 38 - 42℃; for 3h; Temperature; Time; Large scale;
66%
With triethylamine In acetonitrile at 15 - 42℃; Large scale;66%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

dimethyl amine
124-40-3

dimethyl amine

N2,N2-dimethyl-5-nitropyridine-2,6-diamine

N2,N2-dimethyl-5-nitropyridine-2,6-diamine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;100%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

6-iodo-3-nitropyridin-2-amine
351447-13-7

6-iodo-3-nitropyridin-2-amine

Conditions
ConditionsYield
With hydrogen iodide In water at 25℃; for 72h; Inert atmosphere;100%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

para-fluorobenzylamine
140-75-0

para-fluorobenzylamine

2-amino-3-nitro-6-(p-fluoro-benzylamino)-pyridine
33400-49-6

2-amino-3-nitro-6-(p-fluoro-benzylamino)-pyridine

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol for 3h; Reflux; Inert atmosphere;99%
With triethylamine In isopropyl alcohol for 10h; Reflux;98.8%
With triethylamine In methanol at 80℃; for 10h;97.2%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

2-(2-aminoethyl)amino-6-amino-5-nitropyridine
252944-01-7

2-(2-aminoethyl)amino-6-amino-5-nitropyridine

Conditions
ConditionsYield
In methanol; ethyl acetate; ethylenediamine; acetonitrile99%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

3-methyl-benzenemethanamine
100-81-2

3-methyl-benzenemethanamine

N2-(3-methylbenzyl)-5-nitropyridine-2,6-diamine

N2-(3-methylbenzyl)-5-nitropyridine-2,6-diamine

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol for 3h; Reflux; Inert atmosphere;99%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

N,N-diethylpiperidine-3-carboxamide
3367-95-1

N,N-diethylpiperidine-3-carboxamide

1-(6-amino-5-nitropyridin-2-yl)-N,N-diethylpiperidine-3-carboxamide

1-(6-amino-5-nitropyridin-2-yl)-N,N-diethylpiperidine-3-carboxamide

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20 - 110℃;98%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

N6-[(4-methoxyphenyl)methyl]-3-nitropyridine-2,6-diamine

N6-[(4-methoxyphenyl)methyl]-3-nitropyridine-2,6-diamine

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol for 12h; Reflux;98%
With triethylamine In isopropyl alcohol for 3h; Reflux; Inert atmosphere;84%
2,6-diazaspiro[3.3]heptane-2-carboxylic acid tert-butyl ester half oxalate

2,6-diazaspiro[3.3]heptane-2-carboxylic acid tert-butyl ester half oxalate

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

6-(6-amino-5-nitropyridin-2-yl)-2,6-diazaspiro[3.3]heptane-2-carboxylic acid tert-butyl ester

6-(6-amino-5-nitropyridin-2-yl)-2,6-diazaspiro[3.3]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;98%
tert‐butyl 2,5‐diazabicyclo[2.2.2]octane‐2‐carboxylate
858671-91-7

tert‐butyl 2,5‐diazabicyclo[2.2.2]octane‐2‐carboxylate

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

5-(6-amino-5-nitropyridin-2-yl)-2,5-diazabicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester

5-(6-amino-5-nitropyridin-2-yl)-2,5-diazabicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 80℃; for 3h;96.17%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

para-methylbenzylamine
104-84-7

para-methylbenzylamine

N2-(4-methylbenzyl)-5-nitropyridine-2,6-diamine

N2-(4-methylbenzyl)-5-nitropyridine-2,6-diamine

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol for 3h; Reflux; Inert atmosphere;96%
4-fluoro-2-phenethylamine
1583-88-6

4-fluoro-2-phenethylamine

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

N2-(4-fluorophenethyl)-5-nitropyridine-2,6-diamine

N2-(4-fluorophenethyl)-5-nitropyridine-2,6-diamine

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol for 3h; Reflux; Inert atmosphere;96%
With triethylamine In isopropyl alcohol at 120℃; for 0.333333h; Microwave irradiation;90%
1-ethanesulfonylpiperazine
62937-96-6

1-ethanesulfonylpiperazine

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

6-(4-(ethylsulfonyl)piperazin-1-yl)-3-nitropyridin-2-amine

6-(4-(ethylsulfonyl)piperazin-1-yl)-3-nitropyridin-2-amine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 85℃; for 1h;95%
4-acetaminophenol
103-90-2

4-acetaminophenol

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

3-nitro-6-(4-acetamidophenoxy)pyridine-2-ylamine
433226-07-4

3-nitro-6-(4-acetamidophenoxy)pyridine-2-ylamine

Conditions
ConditionsYield
With potassium carbonate In water; N,N-dimethyl-formamide94%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

benzylamine
100-46-9

benzylamine

N6-benzyl-3-nitro-pyridine-2,6-diamine
21626-43-7

N6-benzyl-3-nitro-pyridine-2,6-diamine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 19h;93.8%
With triethylamine In isopropyl alcohol for 3h; Reflux; Inert atmosphere;91%
With triethylamine In 1,4-dioxane
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

6-chloropyridine-2,3-diamine
40851-95-4

6-chloropyridine-2,3-diamine

Conditions
ConditionsYield
With iron; ammonium chloride In water; ethyl acetate at 20℃; for 24h;93.7%
With iron; ammonium chloride In water; isopropyl alcohol at 90℃; for 1h;91%
With sodium tetrahydroborate In ethanol; water at 20℃; for 4h; chemoselective reaction;91%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

(R)-ethyl nipecotate
25137-01-3

(R)-ethyl nipecotate

(R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate

(R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20 - 100℃; for 18h; Solvent; Temperature; Time;93.5%
2,4-Difluoro-benzylamine
72235-52-0

2,4-Difluoro-benzylamine

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

N2-(2,4-difluorobenzyl)-5-nitropyridine-2,6-diamine
157840-46-5

N2-(2,4-difluorobenzyl)-5-nitropyridine-2,6-diamine

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol for 3h; Reflux; Inert atmosphere;93%
With triethylamine In 1,4-dioxane
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

N-(piperidin-4-yl)-(indol-3-yl)acetamide
404018-21-9

N-(piperidin-4-yl)-(indol-3-yl)acetamide

N-(6'-amino-5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-2-(1H-indol-3-yl)-acetamide
404018-25-3

N-(6'-amino-5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-2-(1H-indol-3-yl)-acetamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Heating;93%
(4-Fluoro-benzyl)-methyl-amine
405-66-3

(4-Fluoro-benzyl)-methyl-amine

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

2-amino-6-[(4-fluorobenzyl)(methyl)amino]-3-nitropyridine

2-amino-6-[(4-fluorobenzyl)(methyl)amino]-3-nitropyridine

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol Reflux;93%
7-azaspiro[3.5]decane hydrochloride

7-azaspiro[3.5]decane hydrochloride

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

3-nitro-6-(7-azaspiro[3.5]decane-7-yl)pyridin-2-amine

3-nitro-6-(7-azaspiro[3.5]decane-7-yl)pyridin-2-amine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 80℃; for 12h;93%
1-(2-hydroxyethyl)piperazine
103-76-4

1-(2-hydroxyethyl)piperazine

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

2-[4-(6-amino-5-nitropyridin-2-yl)piperazin-1-yl]ethan-1-ol

2-[4-(6-amino-5-nitropyridin-2-yl)piperazin-1-yl]ethan-1-ol

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol at 110℃; for 0.25h; Microwave irradiation;93%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

6‐amino‐5‐nitropyridine‐2‐thiol

6‐amino‐5‐nitropyridine‐2‐thiol

Conditions
ConditionsYield
With sodium sulfide nonahydrate; sulfur; sodium hydroxide In ethanol for 2.5h; Reflux;92.7%
With sodiumsulfide nonahydrate; sulfur; sodium hydroxide In ethanol for 2.5h; Reflux;92.7%
With sulfur; sodiumsulfide nonahydrate; sodium hydroxide In ethanol Reflux;
acetic anhydride
108-24-7

acetic anhydride

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

2-acetamido-6-chloro-3-nitropyridine
139086-97-8

2-acetamido-6-chloro-3-nitropyridine

Conditions
ConditionsYield
With sulfuric acid; acetic acid for 2h; Heating;92%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

2-amino-5,6-dichloro-3-nitropyridine
203794-33-6

2-amino-5,6-dichloro-3-nitropyridine

Conditions
ConditionsYield
With N-chloro-succinimide; acetic acid at 100℃; for 2h; Temperature; Reagent/catalyst;92%
With chlorine In ethanol at 0℃; for 0.666667h;76%
With chlorine In ethanol at 0℃; for 1h;76%
With N-chloro-succinimide; acetic acid at 100℃; for 2h;46%
2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

2,4-difluoroethynylbenzene
302912-34-1

2,4-difluoroethynylbenzene

6-[2-(2,4-difluorophenyl)ethynyl]-3-nitro-pyridin-2-amine
1380094-28-9

6-[2-(2,4-difluorophenyl)ethynyl]-3-nitro-pyridin-2-amine

Conditions
ConditionsYield
Stage #1: 2-amino-6-chloro-3-nitropyridine With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In acetonitrile at 0 - 5℃; for 0.166667h; Inert atmosphere;
Stage #2: 2,4-difluoroethynylbenzene In acetonitrile at 30℃; for 1h; Product distribution / selectivity;
92%
4-Cyanobenzyl alcohol
874-89-5

4-Cyanobenzyl alcohol

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

4-[[(6-amino-5-nitropyridin-2-yl)oxy]methyl]benzonitrile
1541987-83-0

4-[[(6-amino-5-nitropyridin-2-yl)oxy]methyl]benzonitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h;92%
(R)-N,N-dimethylpiperidine-3-carboxamide hydrochloride

(R)-N,N-dimethylpiperidine-3-carboxamide hydrochloride

2-amino-6-chloro-3-nitropyridine
27048-04-0

2-amino-6-chloro-3-nitropyridine

(R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide

(R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 100℃;91%
With triethylamine In dimethyl sulfoxide at 20 - 110℃; Inert atmosphere;72%

27048-04-0Relevant articles and documents

Flupirtine Analogues: Explorative Synthesis and Influence of Chemical Structure on KV7.2/KV7.3 Channel Opening Activity

Surur, Abdrrahman S.,Beirow, Kristin,Bock, Christian,Schulig, Lukas,Kindermann, Markus K.,Bodtke, Anja,Siegmund, Werner,Bednarski, Patrick J.,Link, Andreas

, p. 41 - 44 (2019)

Neuronal voltage-gated potassium channels KV7.2/KV7.3 are sensitive to small-molecule drugs such as flupirtine, even though physiological response occurs in the absence of ligands. Clinically, prolonged use of flupirtine as a pain medication is associated with rare cases of drug-induced liver injury. Thus, safety concerns prevent a broader use of this non-opioid and non-steroidal analgesic in therapeutic areas with unmet medical needs such as hyperactive bladder or neonatal seizures. With the goal of studying influences of chemical structure on activity and toxicity of flupirtine, we explored modifications of the benzylamino bridge and the substitution pattern in both rings of flupirtine. Among twelve derivatives, four novel thioether derivatives showed the desired activity in cellular assays and may serve as leads for safer KV channel openers.

Synthesis and potassium KV7 channel opening activity of thioether analogues of the analgesic flupirtine

Bock, Christian,Beirow, Kristin,Surur, Abdrrahman S.,Schulig, Lukas,Bodtke, Anja,Bednarski, Patrick J.,Link, Andreas

, p. 8695 - 8699 (2018)

Flupirtine, an opener of neuronal voltage gated potassium channels (KV7.2/3), has been used as a therapeutic alternative for pain treatment in patients refractory to NSAIDs and opioids. Because flupirtine is associated with rare but fatal drug-induced liver injury that may result from the formation of toxic metabolites upon metabolic oxidation, we synthesized novel derivatives with the goal of identifying equally active and ultimately safer KV7.2/3 channel openers. Four thioether analogues were designed to lack a nitrogen atom that would be a prerequisite for the formation of toxic para-quinone diimines, and form sulfoxide and sulfone metabolites instead. KV7.2/3 channel opening activity and hepatotoxicity data of twelve novel flupirtine analogues, four thioethers and their respective sulfoxide and sulfone metabolites are reported.

Pyrido[2,3-b]pyrazine-3(4H)-ketone derivative and application thereof

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Paragraph 0015-0016; 0033, (2021/03/13)

The invention provides a pyrido[2,3-b]pyrazine-3(4H)-ketone derivative and application thereof. The structural general formula of the pyrido[2,3-b]pyrazine-3(4H)-ketone derivative is a formula V, andthe pyrido[2,3-b]pyrazine-3(4H)-ketone derivative comprises pharmaceutically acceptable salt, solvate, hydrate or crystal form thereof. The compound provided by the invention is an active ligand of afibroblast growth factor receptor (FGFR), and research shows that the compound shown in the structure V has good anti-proliferative activity on KATO III gastric cancer cells (FGFR2 amplification) andHuh-7 liver cancer cells (FGFR4 overexpression), and is applied to preparation of drugs for treating tumor-related diseases caused by FGFR abnormal activation as an FGFR inhibitor. The structural general formula V is shown in the description.

NEW HETEROARYL AMIDE DERIVATIVES AS SELECTIVE INHIBITORS OF HISTONE DEACETYLASES 1 AND/OR 2 (HDAC1-2)

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Paragraph 0180, (2020/05/29)

The present invention relates to novel heteroaryl amide derivatives of formula (1) as selective inhibitors of histone deacetylase 1 and 2 (hdac1-2) to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said compounds for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by inhibition the activity of histone deacetylase class I, particularly HDAC1 and HDAC2, such as cancer, neurodegenerative diseases, Infectious diseases, inflammatory diseases, heart failure and cardiac hypertrophy, diabetes, polycystic kidney disease, sickle cell disease and β-thalassemia disease and to methods for the treatment of the disesases mentioned above.

Sulfide Analogues of Flupirtine and Retigabine with Nanomolar KV7.2/KV7.3 Channel Opening Activity

Bock, Christian,Surur, Abdrrahman S.,Beirow, Kristin,Kindermann, Markus K.,Schulig, Lukas,Bodtke, Anja,Bednarski, Patrick J.,Link, Andreas

supporting information, p. 952 - 964 (2019/04/10)

The potassium channel openers flupirtine and retigabine have proven to be valuable analgesics or antiepileptics. Their recent withdrawal due to occasional hepatotoxicity and tissue discoloration, respectively, leaves a therapeutic niche unfilled. Metabolic oxidation of both drugs gives rise to the formation of electrophilic quinones. These elusive, highly reactive metabolites may induce liver injury in the case of flupirtine and blue tissue discoloration after prolonged intake of retigabine. We examined which structural features can be altered to avoid the detrimental oxidation of the aromatic ring and shift oxidation toward the formation of more benign metabolites. Structure–activity relationship studies were performed to evaluate the KV7.2/3 channel opening activity of 45 derivatives. Sulfide analogues were identified that are devoid of the risk of quinone formation, but possess potent KV7.2/3 opening activity. For example, flupirtine analogue 3-(3,5-difluorophenyl)-N-(6-(isobutylthio)-2-(pyrrolidin-1-yl)pyridin-3-yl)propanamide (48) has 100-fold enhanced activity (EC50=1.4 nm), a vastly improved toxicity/activity ratio, and the same efficacy as retigabine in vitro.

Flupirtine and retigabine as templates for ligand-based drug design of KV7.2/3 activators

Surur, Abdrrahman S.,Bock, Christian,Beirow, Kristin,Wurm, Konrad,Schulig, Lukas,Kindermann, Markus K.,Siegmund, Werner,Bednarski, Patrick J.,Link, Andreas

supporting information, p. 4512 - 4522 (2019/05/17)

Drug induced liver injury (DILI) and tissue discoloration led to the recent discontinuation of the therapeutic use of the closely related drugs flupirtine and retigabine, respectively. Experience gained with these drugs strongly suggests that heterotetramer, voltage-gated potassium channels 2 and 3 (KV7.2/3) are valid targets for effective treatment of pain and epilepsy. Because the adverse effects are not related to the mechanism of action, it appears promising to investigate chemical modifications of these clinically validated, drug-like leads. In the present retro-metabolic drug design study, a series of 43 compounds were synthesized and characterized with regard to KV7.2/3 opening activity and efficacy. The most active compound 22d displays excellent potency (EC50 = 4 nM) and efficacy (154%) as a KV7.2/3 opener. Limited aqueous solubility hampered toxicity testing at concentrations higher than 63 μM, but this concentration was nontoxic to two hepatocellular cell lines (HEP-G2 and TAMH) in culture. The slightly less active but more soluble compound 25b (EC50 = 11 nM, efficacy 111%) showed an improved toxicity/activity ratio compared to flupirtine by three orders of magnitude and represents an attractive lead structure for the development of safer analgesics and antiepileptics.

Method for preparing flupirtine hydrochloride

-

Paragraph 0015; 0033; 0038; 0040; 0042; 0043; 0044; 0046, (2019/01/14)

The invention discloses a method for preparing flupirtine hydrochloride. The method comprises the following steps: adopting 2,6-dichloro-3-nitropyridine as an initial material, performing ammonolysis,substituting fluorobenzylamine, purifying, hydrogenating, performing acylation reaction, filtering, precipitating crystals and decompression drying to obtain the flupirtine hydrochloride. The methodis simple in operation, capable of simultaneously performing the hydrogenation and acylation reaction, capable of avoiding the deterioration of polyamino pyridine derivatives as far as possible, capable of titrating ethyl chloroformate without opening a kettle cover, and capable of reducing the harm on the human body.

Discovery of Aromatic Carbamates that Confer Neuroprotective Activity by Enhancing Autophagy and Inducing the Anti-Apoptotic Protein B-Cell Lymphoma 2 (Bcl-2)

Kinarivala, Nihar,Patel, Ronak,Boustany, Rose-Mary,Al-Ahmad, Abraham,Trippier, Paul C.

, p. 9739 - 9756 (2017/12/26)

Neurodegenerative diseases share certain pathophysiological hallmarks that represent common targets for drug discovery. In particular, dysfunction of proteostasis and the resultant apoptotic death of neurons represent common pathways for pharmacological intervention. A library of aromatic carbamate derivatives based on the clinically available drug flupirtine was synthesized to determine a structure-activity relationship for neuroprotective activity. Several derivatives were identified that possess greater protective effect in human induced pluripotent stem cell-derived neurons, protecting up to 80% of neurons against etoposide-induced apoptosis at concentrations as low as 100 nM. The developed aromatic carbamates possess physicochemical properties desirable for CNS therapeutics. The primary known mechanisms of action of the parent scaffold are not responsible for the observed neuroprotective activity. Herein, we demonstrate that neuroprotective aromatic carbamates function to increase the Bcl-2/Bax ratio to an antiapoptotic state and activate autophagy through induction of beclin 1.

A 5 (4H)-pyridone combines furazane oxide synthesis method

-

Paragraph 0034-0035, (2017/04/11)

The invention discloses a synthesis method of 4H-pyridofuroxan-5-one (III, also known as 4H, 5H-(1, 2, 5) oxadiazole (3, 4-b) pyridin-5-one-1-oxide). The synthesis method comprises the following steps (see the following reaction formula): enabling 2-amino-3-nitro-6-chloropyridine (I) to react with potassium (or sodium and the like) fluoride in a water-containing alcohol type solution, or enabling I to react with a nitrite in acetone to prepare 2-amino-3-nitro-6-hydroxypyridine (II); then performing oxidation and condensation reaction under alkaline conditions to prepare III. The synthesis process disclosed by the invention is simple and convenient to operate, and suitable for relatively large-scale production of III; a new way is provided for preparing anti-virus and anti-tumor compounds with the effect of releasing nitric oxide (NO).

QUINOLIUM CONJUGATES OF CYCLOSPORIN

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Page/Page column 26; 27, (2016/03/18)

The present invention relates to conjugates of cyclosporin with quinolium mitochondrial targeting groups, and their therapeutic uses.

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