19798-80-2

Basic information

• Product Name: 2-Amino-4-chloropyridine
• Synonyms: 2-AMINO-4-CHLOROPYRIDINE;4-CHLOROPYRIDIN-2-AMINE;4-CHLORO-PYRIDIN-2-YLAMINE;4-CHLORO-PYRIDINE-2-YLAMINE;4-CHLORO-2-PYRIDINYLAMINE;IFLAB-BB F1926-0004;4-chloro-2-pyridinamine;4-Chloro-2-aminopyridine
• CAS NO: 19798-80-2
• Molecular Formula: C₅H₅ClN₂
• Molecular Weight: 128.56
• EINECS: -0
• Product Categories: PYRIDINE;blocks;Pyridines;Amines and Anilines;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;Heterocyclic Series;pharmacetical;Pyridine series;Amines;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Pharmaceutical intermediate;Amino-pyridine series;Aromatics;Building Blocks;C5;C5 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;OLED materials,pharm chemical,electronic
• Mol File: 19798-80-2.mol
• Article Data: 27

Chemical Properties

• Melting Point: 126-127°C
• Boiling Point: 240.793 °C at 760 mmHg
• Flash Point: 99.428 °C
• Appearance: Colorless to yellow to brown/Liquid
• Density: 1.327 g/cm³
• Vapor Pressure: 0.0372mmHg at 25°C
• Storage Temp.: -20°C Freezer
• Solubility: DMSO, Methanol
• PKA: 5.72±0.11(Predicted)
• Sensitive: Air & Moisture Sensitive
• CAS DataBase Reference: 2-Amino-4-chloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-chloropyridine(19798-80-2)
• EPA Substance Registry System: 2-Amino-4-chloropyridine(19798-80-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 19798-80-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow Cryst

Synthesis Reference(s)

The Journal of Organic Chemistry, 72, p. 4554, 2007 DOI: 10.1021/jo070189y

InChI:InChI=1/C5H5ClN2/c6-4-1-2-8-5(7)3-4/h1-3H,(H2,7,8)/p+1

Synthetic route

tert-butyl (4-chloropyridin-2-yl) carbamate (130721-78-7) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 20℃; for 18h;	100%
With hydrogenchloride In 1,4-dioxane at 20℃; for 18h;	99%
With trifluoroacetic acid In dichloromethane at 20℃;	90%
With hydrogen bromide for 2h;	87%
With hydrogen bromide for 2h; Ambient temperature;

2,2-dimethyl-3-(4-chloropyrid-2-yl)-4-oxo-4H-1,3-benzoxazine (74405-00-8) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
With hydrogenchloride for 8h; Heating;	95%
With hydrogenchloride Hydrolysis;

4-chloropicolinamide (99586-65-9) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
With bromine; potassium hydroxide In water at 90℃; for 2h; Cooling with ice;	84%
With calcium hypochlorite In water at 60 - 80℃; Temperature;	81%
With sodium hydroxide; bromine In water at 80℃; for 1.5h; Hofmann Degradation;	64%

methyl 4-chloropyridine-2-carboxylate hydrochloride → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
With hydrazine hydrate; sodium nitrite In hydrogenchloride; methanol; water; acetic acid	44%
With hydrazine hydrate; acetic acid; sodium nitrite In hydrogenchloride; methanol; water	37 g (60%)

2,4-dichloropyridine (26452-80-2) → 2-Amino-4-chloropyridine (19798-80-2) + 4-Amino-2-chloropyridine (14432-12-3)

Conditions	Yield
With ammonium hydroxide at 170 - 180℃;
With ammonium hydroxide at 180℃;

4-chloro-pyridine-2-carbonyl azide (187973-17-7) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
With acetic acid

N-(4-chloro-2-pyridyl)-1-(2-pyridyl)-1-chloroacetamide → 2-Amino-4-chloropyridine (19798-80-2) + α-chloro-(2-pyridyl)acetic acid

Conditions	Yield
With hydrogenchloride at 60℃; for 3h;	A 70 mg B 45 mg

4-chloro-2-pyridinylisocyanate (1026394-00-2) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
With hydrogenchloride for 48h; Heating; Yield given;

4-chloropyridine-2-carbohydrazide (73771-11-6) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
With hydrogenchloride; acetic acid; sodium nitrite 1.) water, 15 min, 2.) water, heating; Yield given. Multistep reaction;

2,4-dichloropyridine (26452-80-2) + ammonium hydroxide → 2-Amino-4-chloropyridine (19798-80-2) + 4-Amino-2-chloropyridine (14432-12-3)

Conditions	Yield
at 180℃;

C9H13ClN2 → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane; chloroform at 70℃;

4-chloropyridine N-oxide (1121-76-2) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: Ts2O / CHCl3; CH2Cl2 / 0.25 h 2: TFA / CHCl3; CH2Cl2 / 70 °C View Scheme
Multi-step reaction with 2 steps 1: CH2Cl2 / Heating 2: conc. HCl View Scheme
Multi-step reaction with 2 steps 1: 90 percent / CHCl3 / 4 h / Heating 2: 95 percent / conc. HCl / 8 h / Heating View Scheme

4-nitraminopyridine N-oxide (1124-33-0) + zinc-powder → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 20 percent / 1,2-dichloro-ethane / 12 h / Heating 2: 90 percent / CHCl3 / 4 h / Heating 3: 95 percent / conc. HCl / 8 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 8 percent / 1,2-dichloro-ethane / 12 h / Heating 2: 95 percent / conc. HCl / 8 h / Heating View Scheme

4-chloropicolinic acid (5470-22-4) + 4-chloro-6-oxy-picolinic acid → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: diphenylphosphoryl azide, triethylamine / 26 h / Heating 2: 25percent HBr / 2 h / Ambient temperature View Scheme

4-nitraminopyridine N-oxide (1124-33-0) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuryl chloride / 110 °C 2: aqueous NH3 / 180 °C View Scheme

3-deazauracil (626-03-9) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphoryl chloride / 140 °C 2: aqueous NH3 / 180 °C View Scheme

2-(methylcarboxylate)-4-chloro-pyridine + 2-picolinic acid hydrochloride (636-80-6) + methyl 4-chloropyridine-2-carboxylate hydrochloride → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
With thionyl chloride; acetic acid; hydrazine; sodium nitrite In methanol; water

5-bromo-4-chloro-pyridin-2-ylamine (942947-94-6) + bis(pinacol)diborane (73183-34-3) → 2-Amino-4-chloropyridine (19798-80-2) + 4-chloro-5-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))-2-pyridylamine (944401-60-9)

Conditions	Yield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 115℃; for 6.25h; Heating / reflux;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 115℃; for 6h; Inert atmosphere;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 115℃; for 6h; Inert atmosphere;

2-Picolinic acid (98-98-6) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium bromide; thionyl chloride / chlorobenzene / 20.5 h / 50 - 85 °C 2.1: toluene / 1.5 h / 0 - 15 °C 3.1: ammonium hydroxide / 3 h / 20 °C 4.1: bromine; sodium hydroxide / water / 5 h / 20 - 80 °C 4.2: pH 12 - 13 View Scheme
Multi-step reaction with 4 steps 1.1: thionyl chloride / 72 h / Reflux 2.1: toluene / 1 h / 0 - 5 °C 3.1: water / 0.25 h 3.2: 1 h / 20 °C 4.1: sodium hydroxide; bromine / water / 0.58 h / 0 - 5 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium bromide / thionyl chloride / Reflux 1.2: 20 °C 2.1: calcium hypochlorite / water / 60 - 80 °C View Scheme
Multi-step reaction with 4 steps 1: thionyl chloride / Heating / reflux 2: lithium hydroxide; water / tetrahydrofuran / 20 °C 3: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 65 - 100 °C 4: trifluoroacetic acid / dichloromethane / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium bromide; thionyl chloride / 16 h / Reflux 2: ammonium hydroxide / 18 h / 0 - 20 °C 3: bromine; sodium hydroxide / water / 3.5 h / -10 - 100 °C View Scheme

4-Chloro-pyridine-2-carboxylic acid methyl ester (24484-93-3) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ammonium hydroxide / 3 h / 20 °C 2.1: bromine; sodium hydroxide / water / 5 h / 20 - 80 °C 2.2: pH 12 - 13 View Scheme
Multi-step reaction with 2 steps 1.1: water / 0.25 h 1.2: 1 h / 20 °C 2.1: sodium hydroxide; bromine / water / 0.58 h / 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1: lithium hydroxide; water / tetrahydrofuran / 20 °C 2: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 65 - 100 °C 3: trifluoroacetic acid / dichloromethane / 20 °C View Scheme

4-chloropicolinic acid (5470-22-4) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene / 1.5 h / 0 - 15 °C 2.1: ammonium hydroxide / 3 h / 20 °C 3.1: bromine; sodium hydroxide / water / 5 h / 20 - 80 °C 3.2: pH 12 - 13 View Scheme
Multi-step reaction with 2 steps 1.1: thionyl chloride / toluene / 6 h / 80 °C 1.2: 1 h / 20 °C / Cooling with ice 2.1: potassium hydroxide; bromine / water / 2 h / 90 °C / Cooling with ice View Scheme

4-chloro-pyridine-2-carbonyl chloride (53750-66-6) → 2-Amino-4-chloropyridine (19798-80-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene / 1 h / 0 - 5 °C 2.1: water / 0.25 h 2.2: 1 h / 20 °C 3.1: sodium hydroxide; bromine / water / 0.58 h / 0 - 5 °C View Scheme
Multi-step reaction with 2 steps 1: ammonium hydroxide / 18 h / 0 - 20 °C 2: bromine; sodium hydroxide / water / 3.5 h / -10 - 100 °C View Scheme

2-Amino-4-chloropyridine (19798-80-2) → (2-aminopyridin-4-yl)boronic acid (903513-62-2)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 100℃; for 3h; Inert atmosphere;	100%
With potassium acetate; bis(pinacol)diborane; bis(dibenzylideneacetone)-palladium(0); XPhos In 1,4-dioxane at 110℃;

2-Amino-4-chloropyridine (19798-80-2) + 2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (126726-62-3) → 4-(prop-1-en-2-yl)pyridin-2-amine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane; water; acetonitrile at 120℃;	100%
With tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; water; acetonitrile at 90℃; for 12h;

2-Amino-4-chloropyridine (19798-80-2) + 2-azido-1-(4-chlorophenyl)-3-(3,5-dimethoxyphenyl)prop-2-en-1-one → N-(7-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-1-(3,5-dimethoxyphenyl)methanimine

Conditions	Yield
In tetrahydrofuran Reflux;	99.9%

2-Amino-4-chloropyridine (19798-80-2) + acetic anhydride (108-24-7) → N-(4-chloropyridin-2-yl)acetamide

Conditions	Yield
With triethylamine at 20 - 60℃; for 12h;	99%
With triethylamine at 60℃; for 12h;	99%
With pyridine In dichloromethane at 20℃; for 26h;	75%

2-Amino-4-chloropyridine (19798-80-2) → N-nitro-2-amino-4-chloropyridine (24484-97-7)

Conditions	Yield
With sulfuric acid; nitric acid at 0 - 5℃; for 78h;	99%
With sulfuric acid; nitric acid at 0 - 20℃; for 0.333333h;	92%
With sulfuric acid; nitric acid at 0℃; for 0.333333h;

2-Amino-4-chloropyridine (19798-80-2) + pivaloyl chloride (3282-30-2) → 4-chloro-2-trimethylacetamidopyridine (188577-70-0)

Conditions	Yield
With pyridine at 0 - 20℃; for 12h;	99%
With pyridine at 0 - 20℃; for 12h;	99%
With pyridine for 12h; Ambient temperature;	95%

2-Amino-4-chloropyridine (19798-80-2) + phenyl chloroformate (1885-14-9) → phenyl N-(4-chloro-2-pyridyl)-N-phenoxycarbonylcarbamate (670253-26-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 25℃; for 2h;	99%
With triethylamine In tetrahydrofuran at 20℃; for 1.5h;	53.4%

2-Amino-4-chloropyridine (19798-80-2) + dimethyl amine (124-40-3) → 2-amino-4-(dimethylamino)-pyridine (50426-31-8)

Conditions	Yield
In water at 120℃; Microwave irradiation;	99%
In water at 175℃; for 0.583333h; Microwave;	94%
Stage #1: 2-Amino-4-chloropyridine; dimethyl amine In water at 175℃; for 0.583333h; Microwave irradiation; Stage #2: With ammonium carbonate In water; acetonitrile	94%
In water at 175℃; for 0.583333h; Microwave irradiation;	94%

2-Amino-4-chloropyridine (19798-80-2) → 5-bromo-4-chloro-pyridin-2-ylamine (942947-94-6)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile for 14h;	99%
With N-Bromosuccinimide In acetonitrile at 20℃; for 14h;	99%
With N-Bromosuccinimide In acetonitrile at 20℃;	99%

2-Amino-4-chloropyridine (19798-80-2) + cyclopropylboronic acid (411235-57-9) → 2-amino-4-(cyclopropyl)pyridine (908269-97-6)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tricyclohexylphosphine In 1,4-dioxane; acetonitrile at 120℃; Inert atmosphere;	99%
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 80℃; for 15h;

2-Amino-4-chloropyridine (19798-80-2) + 4-(chlorosulfonyl)benzenesulfonyl fluoride → 4-(N-(4-chloropyridin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride

Conditions	Yield
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction;	99%

2-Amino-4-chloropyridine (19798-80-2) + tert-butyl (azetidin-3-ylmethyl)carbamate hydrochloride (1170108-38-9) → tert-butyl ((1-(2-aminopyridin-4-yl)azetidin-3-yl)methyl)carbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 120℃; for 24h; Sealed tube;	96%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 120℃; for 24h; Sealed tube;

2-Amino-4-chloropyridine (19798-80-2) + Methoxyacetyl chloride (38870-89-2) → N-(4-chloro-2-pyridyl)-2-methoxyacetamide (1262776-53-3)

Conditions	Yield
With triethylamine In dichloromethane at 20 - 25℃; for 0.25h;	96%

2-Amino-4-chloropyridine (19798-80-2) + ibuprofen (15687-27-1) → N-(4-chloro-pyridin-2-yl)-2-(4-isobutyl-phenyl)-propionamide

Conditions	Yield
Stage #1: ibuprofen With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: 2-Amino-4-chloropyridine In dichloromethane for 72h; Heating;	95%

2-Amino-4-chloropyridine (19798-80-2) + ethyl (2E)-3-dimethylamino-2-(1H-indol-3-yl)propenoate (714274-03-0) → 7-chloro-3-(1H-indol-3-yl)-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions	Yield
With acetic acid for 4h; Heating;	95%

2-Amino-4-chloropyridine (19798-80-2) + 3-pyridylboronic acid (1692-25-7) → 4-(pyridin-3-yl)pyridin-2-amine (865604-20-2)

Conditions	Yield
With potassium phosphate; PdCl2[P(tBu)2(p-Me2NC6H4)]2 In 1,4-dioxane; water at 100℃; Suzuki-Miyaura cross-coupling;	95%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In acetonitrile at 170℃; Suzuki reaction; Microwave irradiation;	95%

2-Amino-4-chloropyridine (19798-80-2) + Ethoxycarbonyl isothiocyanate (16182-04-0) → ethyl [(4-chloropyridin-2-yl)carbamothioyl]carbamate (1131410-83-7)

Conditions	Yield
In 1,4-dioxane at 20℃;	95%
In 1,4-dioxane at 25℃; for 2h;	92.1%
In 1,4-dioxane at 20℃; for 2h;	16.5 g
In 1,4-dioxane at 20℃; for 2h;	8.5 g

2-Amino-4-chloropyridine (19798-80-2) + (2-methoxyphenyl)methanol (612-16-8) → C13H11ClN2O2

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) iodide In water at 20℃; for 6h;	95%

2-Amino-4-chloropyridine (19798-80-2) + 3-chlorobenzoate (535-80-8) → 3-chloro-N-(4-chloropyridin-2-yl)benzamide (901390-17-8)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	94%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane

2-Amino-4-chloropyridine (19798-80-2) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → 4-(2-(2-methoxyethoxy)ethoxy)pyridin-2-amine

Conditions	Yield
Stage #1: 2-(2-methoxyethoxy)ethyl alcohol With sodium hydride In neat (no solvent) for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: 2-Amino-4-chloropyridine In neat (no solvent) at 120℃; for 16h; Sealed tube;	94%

2-Amino-4-chloropyridine (19798-80-2) + (N,N-dimethylamino)dimethylchlorosilane (18209-60-4) → C9H16ClN3Si

Conditions	Yield
Stage #1: 2-Amino-4-chloropyridine With n-butyllithium In hexane at 0 - 20℃; for 12h; Inert atmosphere; Schlenk technique; Stage #2: (N,N-dimethylamino)dimethylchlorosilane In hexane at 0 - 20℃; for 12h; Inert atmosphere; Schlenk technique;	94%

2-Amino-4-chloropyridine (19798-80-2) + tert-butylisonitrile (119072-55-8, 7188-38-7) + Glyoxilic acid (298-12-4) → C11H14ClN3 (1329425-87-7)

Conditions	Yield
Stage #1: 2-Amino-4-chloropyridine; Glyoxilic acid With perchloric acid In methanol Groebke-Blackburn-Bienayme reaction; Stage #2: tert-butylisonitrile In methanol at 20℃; for 12h; Groebke-Blackburn-Bienayme reaction; regioselective reaction;	93%

2-Amino-4-chloropyridine (19798-80-2) + benzyl alcohol (100-51-6) → N-(4-chloropyridin-2-yl)benzamide

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) iodide In water at 20℃; for 6h;	93%

2-Amino-4-chloropyridine (19798-80-2) → 2-bromo-4-chloropyridine (22918-01-0)

Conditions	Yield
Stage #1: 2-Amino-4-chloropyridine With hydrogen bromide; bromine In water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In water at -10 - 20℃; Stage #3: With sodium hydroxide In water at 0℃; pH=> 10;	92%
Stage #1: 2-Amino-4-chloropyridine With hydrogen bromide; bromine In water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In water at -10 - 20℃; Stage #3: With sodium hydroxide In water at 0℃; pH=10;	92%
Stage #1: 2-Amino-4-chloropyridine With hydrogen bromide; bromine In water at -5℃; for 0.333333h; Stage #2: With sodium nitrite In water at -5℃; for 0.5h;	40%

2-Amino-4-chloropyridine (19798-80-2) + tert-butyl N-(4-piperidinylmethyl)carbamate (135632-53-0) → tert-butyl ((1-(2-aminopyridin-4-yl)piperidin-4-yl)methyl)carbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 120℃; for 24h; Sealed tube;	92%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 120℃; for 24h; Sealed tube;

2-Amino-4-chloropyridine (19798-80-2) + ortho-bromobenzaldehyde (6630-33-7) → 2-(4-chloropyridin-2-yl)-2H-indazole

Conditions	Yield
With choline azide; caesium carbonate at 20℃; for 4h; Green chemistry;	92%

4,4-dimethylpiperidine (4045-30-1) + 2-Amino-4-chloropyridine (19798-80-2) → 4-(4,4-dimethylpiperidin-1-yl)pyridin-2-amine

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 200℃; for 0.75h; Microwave irradiation;	92%

2-Amino-4-chloropyridine (19798-80-2) → 4-chloro-5-iodopyridin-2-ylamine (670253-37-9)

Conditions	Yield
With N-iodo-succinimide In N,N-dimethyl-formamide for 43h; regioselective reaction;	90%
With N-iodo-succinimide In N,N-dimethyl-formamide at 40℃;	70%
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 18h;	62%

Upstream product

• 53750-66-6 4-chloro-pyridine-2-carbonyl chloride 
• 5470-22-4 4-chloropicolinic acid 
• 24484-93-3 4-Chloro-pyridine-2-carboxylic acid methyl ester 
• 98-98-6 2-Picolinic acid 
• 942947-94-6 5-bromo-4-chloro-pyridin-2-ylamine 
• 73183-34-3 bis(pinacol)diborane 
• 636-80-6 2-picolinic acid hydrochloride 
• 176977-85-8 methyl 4-chloropyridine-2-carboxylate hydrochloride 
• 626-03-9 3-deazauracil 
• 1124-33-0 4-nitraminopyridine N-oxide 
• 99586-65-9 4-chloropicolinamide 
• 26452-80-2 2,4-dichloropyridine 
• 73771-11-6 4-chloro-pyridine-2-carboxylic acid hydrazide 
• 1026394-00-2 4-chloro-2-pyridinylisocyanate 

Downstream Products

• 84487-08-1 4-methoxy-3-nitro-pyridin-2-ylamine 
• 864245-22-7 4-(3-methyl-4-nitrophenoxy)pyridin-2-ylamine 
• 55933-91-0 2-amino-3,4,5-trichloropyridine 
• 188577-70-0 4-chloro-2-trimethylacetamidopyridine 
• 6980-08-1 4-chloro-3-nitro-2-pyridinamine 
• 24484-96-6 2-amino-4-chloro-5-nitropyridine 
• 274-76-0 imidazo[1,2-a]pyridine 
• 192654-11-8 10-chloro-5,6-dihydro-5,6-dioxonaphtho-[1',2':4,5]imidazo[1,2-a]pyridine 
• 864244-67-7 4-(2-fluoro-4-nitro-phenoxy)pyridin-2-amine 
• 417723-45-6 4-(4-nitrophenoxy)pyridin-2-amine 
• 864245-27-2 4-(4-Nitro-3-trifluoromethylphenoxy)pyridin-2-ylamine 
• 864244-98-4 4-(2-methyl-4-nitrophenoxy)pyridin-2-amine 
• 670253-37-9 4-chloro-5-iodopyridin-2-ylamine 
• 670253-31-3 5-(2-Aminopyridin-4-ylamino)indole-1-carboxylic acid phenylamide 

Relevant articles and documents

Synthesis and biological evaluation of novel 4-(2-fluorophenoxy)-2-(1h- tetrazol-1-yl)pyridines bearing semicarbazone moieties as potent antitumor agents

A series of 4-(2-fluorophenoxy)-2-(1H-tetrazol-1-yl)pyridines bearing semicarbazone moieties were synthesized and evaluated for their in vitro antitumor potency. Some of the compounds (10b, 10c, 10e-10h, 10m-10p, 10r, and 11b) exhibited moderate to excellent antitumor activity as compared to sorafenib and PAC-1, as well as low levels of toxicity toward the human fetal lung fibroblast cell line WI-38. The most promising compound 10p (IC50 = 0.08, 0.36, 0.97 μM) was 45.1-, 6.1-, and 2.4-fold more active than sorafenib (IC50 = 3.61, 2.19, 2.32 μM), and 17, 3.2, and 2.9 times better than PAC-1 (IC50 = 1.36, 1.17, 2.83 μM) against three cancer cell lines (HT-29, H460, and MKN-45), respectively. In addition, further studies examining enzymatic activity suggested that the marked pharmacological activity observed might be ascribed to an inhibitory action against CRAf kinase. A series of 4-(2-fluorophenoxy)-2-(1H-tetrazol-1-yl)pyridines bearing semicarbazone moieties were synthesized and evaluated for their cytotoxic activities in vitro. The most promising compound 10p was further examined for enzymatic activity, with the goal to investigate the molecular mechanisms of action.

Synthesis method of imidazopyridine or pyrimidine derivative

The invention belongs to the technical field of synthesis, and particularly relates to a synthesis method of an imidazopyridine or pyrimidine derivative. The imidazopyridine or pyrimidine compound is obtained by taking pyridine or pyrimidinecarboxylic acid as a synthon through amidation, Hofmann degradation and cyclization reaction, and the obtained imidazopyridine or pyrimidine derivative can be further converted to generate a functional product. The method has the advantages of easily available raw materials, simple operation, high reaction efficiency, convenient post-treatment, and diversity of functional groups.

Preparation method of 2-amino-4-fluoropyridine

The invention discloses a preparation method of 2-amino-4-fluoropyridine, comprising the synthetic steps of 1, subjecting 2-pyridinecarboxylic acid as a raw material to reaction in the presence of thionyl chloride and a salt to obtain 4-chloropyridine-2-acyl chloride, and subjecting 4-chloropyridine-2-acyl chloride the presence of ammonia to obtain 4-chloropyridine-2-amide; 2, subjecting 4-chloropyridine-2-amide to Hofmann rearrangement reaction to obtain 2-amino-4-chloropyridine; 3, subjecting 2-amino-4-chloropyridine to halogen exchange to obtain 2-amino-4-fluoropyridine. The problems of theexisting preparation method, such as long synthetic path, operational complexity, high pollution of three wastes, poor atomic economy, low yield and high manufacture cost, are solved.

ANTIVIRAL DRUGS FOR TREATMENT OF ARENA VIRUS INFECTION

Compounds, methods and pharmaceutical compositions for treating viral infections, by administering certain compounds in therapeutically effective amounts are disclosed. Methods for preparing the compounds and methods of using the compounds and pharmaceutical compositions thereof are also disclosed. In particular, the treatment and prophylaxis of viral infections such as caused by the Arenavirus family such as Lassa fever, Argentine hemorrhagic fever, Bolivian hemorrhagic fever, and Venezuelan hemorrhagic fever