5469-70-5

Basic information

• Product Name: Pyridazin-3-amine
• Synonyms: 3-AMINOPYRIDAZINE,98.0+%(GC)(T);Pyridazin-3-ylamine;pyridazin-3-amine hydrochloride;Pyridazin-2-amine;Pyridazin-3-aMine/3-AMinopyridazine;Pyridazin-3-amine, 3-Amino-1,2-diazine;PYRIDAZIN-3-AMINE;3-AMINOPYRIDAZINE
• CAS NO: 5469-70-5
• Molecular Formula: C₄H₅N₃
• Molecular Weight: 95.1
• Product Categories: Amines;Pyrazines, Pyrimidines & Pyridazines;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Pyridazines;Heterocycles
• Mol File: 5469-70-5.mol

Chemical Properties

• Melting Point: 171 °C
• Boiling Point: 326.19 °C at 760 mmHg
• Flash Point: 177.256 °C
• Appearance: White to pale yellow/Solid
• Density: 1.216 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 4.88±0.10(Predicted)
• CAS DataBase Reference: Pyridazin-3-amine(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridazin-3-amine(5469-70-5)
• EPA Substance Registry System: Pyridazin-3-amine(5469-70-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Safety Statements: 26-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5469-70-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Pyridazin-3-amine is used as a building block in the synthesis of various organic compounds. Its unique structure allows for the formation of diverse chemical entities, making it a valuable intermediate in the development of new organic molecules.
Used in Pharmaceuticals:
Pyridazin-3-amine is used as a key intermediate in the synthesis of pharmaceutical compounds. Its presence in the molecular structure can impart specific biological activities, making it a crucial component in the development of new drugs.
Used in Agrochemicals:
Pyridazin-3-amine is used as a raw material in the production of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds can enhance their effectiveness in controlling pests and weeds, thereby improving crop yields.
Used in Dyestuffs:
Pyridazin-3-amine is used in the synthesis of dyes and pigments. Its ability to form colored compounds makes it a valuable component in the production of various dyestuffs, which are used in industries such as textiles, plastics, and printing inks.

InChI:InChI=1/C4H5N3.ClH/c5-4-2-1-3-6-7-4;/h1-3H,(H2,5,7);1H

Synthetic route

6-chloro-pyridazin-3-ylamine (5469-69-2) → 3-aminopyridazine (5469-70-5)

Conditions	Yield
With sodium hydroxide; hydrogen; palladium 10% on activated carbon In tetrahydrofuran; water at 20℃; for 48h;	100%
With palladium on activated charcoal; hydrogen; sodium hydroxide In ethanol at 20℃; under 760.051 Torr; for 20h;	100%
With hydrogen; sodium hydroxide; palladium 10% on activated carbon In ethanol at 20℃; for 18h;	99.5%

3-chloropyridazine (1120-95-2) → 3-aminopyridazine (5469-70-5)

Conditions	Yield
With ammonium hydroxide In tetrahydrofuran at 150℃; for 36h;	50%
With ammonia at 180℃; under 117681 Torr;
With methanol; ammonia at 175℃;
With ethanol; ammonia at 175℃;

6-bromopyridazin-3-amine (88497-27-2) → 3-aminopyridazine (5469-70-5)

Conditions	Yield
With sodium hydroxide; palladium on activated charcoal Hydrogenation;

3-hydrazinyl pyridazine (40972-16-5) → 3-aminopyridazine (5469-70-5)

Conditions	Yield
With hydrogen; nickel for 2.5h;

9-tert-butylfluorene (17114-78-2) + C4H4N3(1-)*K(1+) → 3-aminopyridazine (5469-70-5) + potassium salt of 9-tert-butylfluorene (106358-48-9)

Conditions	Yield
In dimethyl sulfoxide at 24.9℃; Equilibrium constant;

4-aminopyridazine (20744-39-2) → 3-aminopyridazine (5469-70-5)

Conditions	Yield
palladium on charcoal In sodium hydroxide; ethanol

3-aminopyridazine (5469-70-5) + methyl 2-(4-(4-(4-(tert-butoxycarbonylamino)phenyl)thieno[3,2-d]pyrimidin-7-yl)phenyl)acetate (1421230-72-9) → 2-(4-(4-(4-(3-pyridazin-3-ylureido)phenyl)thieno[3,2-d]pyrimidin-7-yl)phenyl)acetic acid (1421230-37-6)

Conditions	Yield
Stage #1: 3-aminopyridazine; methyl 2-(4-(4-(4-(tert-butoxycarbonylamino)phenyl)thieno[3,2-d]pyrimidin-7-yl)phenyl)acetate With 4-Nitrophenyl chloroformate In 1,4-dioxane at 20℃; Stage #2: With water In tetrahydrofuran; methanol	100%

3-aminopyridazine (5469-70-5) + perfluorophenyl 1-(4-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate → 1-(4-bromo-2-methoxyphenyl)-2-oxo-N-(pyridazin-3-yl)-1,2-dihydroquinoline-6-sulfonamide

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.333333h;	100%

3-aminopyridazine (5469-70-5) + 2-chloroethanal (107-20-0) → imidazo[1.2-b]pyridazine (766-55-2)

Conditions	Yield
at 70℃;	100%
In water; ethyl acetate at 85℃; for 2h; Solvent; Temperature;
In methanol; water at 87℃; for 1h; Solvent; Temperature; Concentration;

3-aminopyridazine (5469-70-5) + (5-bromo-pyridin-3-yl)-carbamic acid tert-butyl ester (361550-43-8) → tert-butyl (5-(pyridazin-3-ylamino)pyridin-3-yl)carbamate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; caesium carbonate In 1,4-dioxane at 90℃; for 16h; Inert atmosphere;	98%

3-aminopyridazine (5469-70-5) + 2,3-dibromopyridine (13534-89-9) → pyrido[3',2':4,5]imidazo[1,2-b]pyridazine + pyrido[2',3':4,5]imidazo[1,2-b]pyridazine

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,2-dimethoxyethane at 140℃; for 30h;	A n/a B 97%

3-aminopyridazine (5469-70-5) + ortho-methylbenzoic acid (118-90-1) → 2-methyl-N-(pyridazin-3-yl)benzamide

Conditions	Yield
Stage #1: ortho-methylbenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 3-aminopyridazine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	96%

3-aminopyridazine (5469-70-5) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N,N-dimethyl-N'-pyridazin-3-yl-formamidine (35053-54-4)

Conditions	Yield
for 2h; Reflux;	95%
In toluene at 20 - 85℃;	91%
In toluene at 20 - 85℃;	91%
In toluene for 2h; Heating;
In methanol at 45℃; for 6h; Solvent; Temperature;

3-aminopyridazine (5469-70-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-dimethyl-N'-pyridazin-3-yl-formamidine (35053-54-4)

Conditions	Yield
In N,N-dimethyl acetamide for 2h; Reflux;	95%

3-aminopyridazine (5469-70-5) + Methyl (Z)-2-<(benzyloxycarbonyl)amino>-3-dimethylaminopropenoate (219739-90-9) → 3-<(Benzyloxycarbonyl)amino>-4H-pyrimido<1,2-b>pyridazin-4-one (225112-17-4)

Conditions	Yield
With acetic acid for 6h; Reflux;	93%
With sodium acetate; acetic acid 1.) reflux, 3.5 h, 2.) reflux, 4 h; Yield given; Multistep reaction;

3-aminopyridazine (5469-70-5) + 2-chloro-3-iodo-quinoline (128676-85-7) → pyridazino[6',1':2,3]imidazo[4,5-b]quinoline

Conditions	Yield
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate In toluene for 17h; Heating;	93%

3-aminopyridazine (5469-70-5) + 1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)-sulfonyl)methanesulfonamide (145100-50-1) → 3-N'-monotrifluoromethanesulfonamidopyridazine

Conditions	Yield
In acetonitrile at 60℃; Inert atmosphere;	90%

3-aminopyridazine (5469-70-5) + phenyl chloroformate (1885-14-9) → phenyl pyridazin-3-ylcarbamate (1020327-61-0)

Conditions	Yield
With pyridine In acetonitrile at 0℃; for 1h;	87%
With pyridine In acetonitrile at 0 - 20℃;	74%
With pyridine In tetrahydrofuran; acetonitrile Product distribution / selectivity;	70%

3-aminopyridazine (5469-70-5) + methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate (125008-68-6) → 3-benzoylamino-4H-pyrimido[1,2-b]pyrdazin-4-one

Conditions	Yield
With acetic acid for 4.5h; Condensation; Heating;	86%

3-aminopyridazine (5469-70-5) + 2-chloro-6-methylphenyl isothiocyanate (19241-34-0) → 1-(2-Chloro-6-methyl-phenyl)-3-pyridazin-3-yl-thiourea

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1) 0 deg C to r.t., 2) r.t., 3 h;	85%

3-aminopyridazine (5469-70-5) + 2,3-dibromoquinoline (13721-00-1) → 3-bromo-N-(pyridazin-3-yl)quinolin-2-amine

Conditions	Yield
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,2-dimethoxyethane for 7h; Heating;	84%

3-aminopyridazine (5469-70-5) + (P)-perfluorophenyl 1-(5-fluoro-2-methoxy-4-(3,3,3-trifluoropropyl)phenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate → (P)-1-(5-fluoro-2-methoxy-4-(3,3,3-trifluoropropyl)phenyl)-2-oxo-N-(pyridazin-3-yl)-1,2-dihydroquinoline-6-sulfonamide

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; dimethyl sulfoxide for 0.25h; Cooling with ice;	84%

3-aminopyridazine (5469-70-5) + 2,6-dichlorobenzenesulfonyl chloride (6579-54-0) → 9-chlorobenzo[e]pyridazino[1,6-b][1,2,4]thiadiazine 10,10-dioxide

Conditions	Yield
Stage #1: 3-aminopyridazine; 2,6-dichlorobenzenesulfonyl chloride With potassium carbonate In acetonitrile at 20℃; for 10h; Stage #2: With copper(l) iodide In acetonitrile at 80℃; for 3h; Ullmann Condensation; chemoselective reaction;	84%

3-aminopyridazine (5469-70-5) + 2-chloro-6-methylphenyl isocyanate (40398-01-4) → 1-(2-Chloro-6-methyl-phenyl)-3-pyridazin-3-yl-urea

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1) 0 deg C to r.t., 2) r.t., 3 h;	83%

3-aminopyridazine (5469-70-5) + [1,2,4]Oxadiazolo[2,3-b]pyridazine-2-thione (71344-17-7) → 1,3-di(3-pyridazinyl)urea (71344-18-8)

Conditions	Yield
In dimethyl sulfoxide at 80 - 90℃; for 2h;	82%

3-aminopyridazine (5469-70-5) + dichlorobenzenesulfonyl chloride (82417-45-6) → 6-chlorobenzo[e]pyridazino[1,6-b][1,2,4]thiadiazine 10,10-dioxide

Conditions	Yield
Stage #1: 3-aminopyridazine; dichlorobenzenesulfonyl chloride With potassium carbonate In acetonitrile at 20℃; for 10h; Stage #2: With copper(l) iodide In acetonitrile at 80℃; for 3h; Ullmann Condensation; chemoselective reaction;	82%

3-aminopyridazine (5469-70-5) + 2,3-dibromopyridine (13534-89-9) → N-(3-bromopyridin-2-yl)pyridazin-3-amine

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,2-dimethoxyethane for 7h; Heating;	81%

3-aminopyridazine (5469-70-5) + 3-(5-bromo-pyridin-2-yloxy)-azetidine-1-carboxylic acid 4-nitro-phenyl ester (1186234-54-7) → 3-(5-bromo-pyridin-2-yloxy)-azetidine-1-carboxylic acid pyridazin-3-ylamide (1186234-62-7)

Conditions	Yield
Stage #1: 3-aminopyridazine With sodium hydride In N,N-dimethyl-formamide; mineral oil Inert atmosphere; Cooling with ice; Stage #2: 3-(5-bromo-pyridin-2-yloxy)-azetidine-1-carboxylic acid 4-nitro-phenyl ester In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; Cooling with ice;	80%

3-aminopyridazine (5469-70-5) + 2-iodopyrazine (32111-21-0) → C8H7N5

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 3h; Inert atmosphere;	80%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 3h; Inert atmosphere;	80%
Stage #1: 3-aminopyridazine; 2-iodopyrazine With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane for 0.166667h; Inert atmosphere; Stage #2: With tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 90℃; for 3h;	80%

3-aminopyridazine (5469-70-5) + 2-chloro-3-(2-(methylthio)benzo[d]thiazol-6-yl)propanal → 6-(imidazo[1,2-b]pyridazin-3-ylmethyl)-2-(methylthio)benzo[d]thiazole

Conditions	Yield
In butan-1-ol for 15h; Reflux;	80%

3-aminopyridazine (5469-70-5) + 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6) + (3S)-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (1398752-89-0) → Phenylmethyl (3S)-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-3-[(3-pyridazinylamino)carbonyl]-1-pyrazolidinecarboxylate (1398753-00-8)

Conditions	Yield
With 4-methyl-morpholine In acetonitrile	79%

3-aminopyridazine (5469-70-5) + C21H25FO3 → 3-((13S,15R)-3-fluoro-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl)-N-(pyridazin-3-yl)propanamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 50℃; for 3.5h;	79%
With pyridine; triphenylphosphine In dichloromethane; ethyl acetate at 20℃; Inert atmosphere;

Upstream product

• 1120-95-2 3-chloropyridazine 
• 5469-69-2 6-chloro-pyridazin-3-ylamine 
• 88497-27-2 6-bromopyridazin-3-amine 
• 40972-16-5 3-hydrazinyl pyridazine 
• 17114-78-2 9-tert-butylfluorene 
• 20744-39-2 4-aminopyridazine 

Downstream Products

• 515-62-8 4-amino-N-pyridazin-3-yl-benzenesulfonamide 
• 106840-27-1 N-acetyl-sulfanilic acid pyridazin-3-ylamide 
• 147362-90-1 tert-butyl N-(3-pyridazinyl)carbamate 
• 1844-54-8 2-phenylimidazo<1,2-b>pyridazine 
• 17114-78-2 9-tert-butylfluorene 
• 123531-27-1 ethyl imidazo[1,2-b]pyridazine-2-carboxylate 
• 225112-17-4 3-<(Benzyloxycarbonyl)amino>-4H-pyrimido<1,2-b>pyridazin-4-one 

Relevant articles and documents

Development of new highly potent imidazo[1,2-b[pyridazines targeting Toxoplasma gondii calcium-dependent protein kinase 1

Using a structure-based design approach, we have developed a new series of imidazo[1,2-b]pyridazines, targeting the calcium-dependent protein kinase-1 (CDPK1) from Toxoplasma gondii. Twenty derivatives were thus synthesized. Structure-activity relationships and docking studies confirmed the binding mode of these inhibitors within the ATP binding pocket of TgCDPK1. Two lead compounds (16a and 16f) were then identified, which were able to block TgCDPK1 enzymatic activity at low nanomolar concentrations, with a good selectivity profile against a panel of mammalian kinases. The potential of these inhibitors was confirmed in vitro on T. gondii growth, with EC50 values of 100 nM and 70 nM, respectively. These best candidates also displayed low toxicity to mammalian cells and were selected for further in vivo investigations on murine model of acute toxoplasmosis.

HETEROCYCLIC COMPOUNDS AND USES THEREOF

Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.

IMIDAZOTRIAZINONE COMPOUNDS

The present invention provides imidazotriazinone compounds which are inhibitors of phosphodiesterase 9 and pharmaceutically acceptable salt thereof. The present invention further provides processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of PDE9 associated diseases or disorders in mammals, including humans.

TRIAZOLO- AND PYRAZOLOQUINAZOLINE DERIVATIVES AS PDE10A ENZYME INHIBITOR

The invention relates to compounds of the formula (I) and their use as pharmaceutical ingredients, in particular for the treatment of CNS related diseases.

IMIDAZOTRIAZINONE COMPOUNDS

The present invention provides imidazotriazinone compounds which are inhibitors of phosphodiesterase 9. The present invention further provides processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of PDE9 associated diseases or disorders in mammals, including CNS or neurodegeneration disorder.

Competitive antagonism of insect GABA receptors by iminopyridazine derivatives of GABA

A series of 4-(6-imino-3-aryl/heteroarylpyridazin-1-yl)butanoic acids were synthesized and examined for antagonism of GABA receptors from three insect species. When tested against small brown planthopper GABA receptors, the 3,4-methylenedioxyphenyl and the 2-naphthyl analogues showed complete inhibition of GABA-induced fluorescence changes at 100 μM in assays using a membrane potential probe. Against common cutworm GABA receptors, these analogues displayed approximately 86% and complete inhibition of GABA-induced fluorescence changes at 100 μM, respectively. The 4-biphenyl and 4-phenoxyphenyl analogues showed moderate inhibition at 10 μM in these receptors, although the inhibition at 100 μM was not complete. Against American cockroach GABA receptors, the 4-biphenyl analogue exhibited the greatest inhibition (approximately 92%) of GABA-induced currents, when tested at 500 μM using a patch-clamp technique. The second most active analogue was the 2-naphthyl analogue with approximately 85% inhibition. The 3-thienyl analogue demonstrated competitive inhibition of cockroach GABA receptors. Homology modeling and ligand docking studies predicted that hydrophobic 3-substituents could interact with an accessory binding site at the orthosteric binding site.

PYRIMIDINYL AND 1,3,5-TRIAZINYL BENZIMIDAZOLES AND THEIR USE IN CANCER THERAPY

Provided herein are pyrimidinyl and 1,3,5-triazinyl benzimidazoles of Formula I, and their pharmaceutical compositions, preparation, and use as agents or drugs for cancer therapy, either alone or in combination with radiation and/or other anticancer drugs.

7-AZASPIRO[3.5]NONANE-7-CARBOXAMIDE COMPOUNDS

Provided herein are 7-azaspiro[3.5]nonane-7-carboxamide compounds and the pharmaceutically acceptable salts of such compounds useful in treating diseases or conditions associated with fatty acid amide hydrolase (FAAH) activity, conditions including including acute pain, chronic pain, neuropathic pain, nociceptive pain, inflammatory pain, cancer and cancer pain, fibromyalgia, rheumatoid arthritis, inflammatory bowel disease, lupus, diabetes, allergic asthma, vascular inflammation, urinary incontinence, overactive bladder, emesis, cognitive disorders, anxiety, depression, sleeping disorders, eating disorders, movement disorders, glaucoma, psoriasis, multiple sclerosis, cerebrovascular disorders, brain injury, gastrointestinal disorders, hypertension, or cardiovascular disease

1-OXA-8-AZASPIRO [4, 5 ] DECANE- 8 -CARBOXAMIDE COMPOUNDS AS FAAH INHIBITORS

Provided herein are 1-oxa-8-azaspiro[4.5]decane-8-carboxamide compounds of formula I wherein Ar1, Ar2, R1, R2, R3 and R4 are as defined herein and the pharmaceutically acceptable salts of such compounds useful in treating diseases or conditions associated with fatty acid amide hydrolase (FAAH) activity, conditions including acute pain, chronic pain, neuropathic pain, nociceptive pain, inflammatory pain, fibromyalgia, rheumatoid arthritis, inflammatory bowel disease, lupus, diabetes, allergic asthma, vascular inflammation, urinary incontinence, overactive bladder, emesis, cognitive disorders, anxiety, depression, sleeping disorders, eating disorders, movement disorders, glaucoma, psoriasis, multiple sclerosis, cerebrovascular disorders, brain injury, gastrointestinal disorders, hypertension, or cardiovascular disease.

4-BENZYLIDENE-3-METHYLPIPERIDINE ARYL CARBOXAMIDE COMPOUNDS USEFUL AS FAAH INHIBITORS

The present invention relates to compounds of Formula (I) wherein Ar is optionally substituted phenyl or heteroaryl; or a pharmaceutically acceptable salt thereof; processes for the preparation of the compounds; intermediates used in the preparation of the compounds; compositions containing the compounds; and uses of the compounds in treating diseases or conditions associated with fatty acid amide hydrolase (FAAH) activity.