1722-10-7

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Chloro-6-methoxypyridazine is used as a key intermediate in the preparation of a number of α-aryl-α-(pyridazin-3-yl)-acetonitriles. These compounds are important in the development of various pharmaceutical products due to their potential therapeutic properties.
Used in the Synthesis of Minaprine:
In the specific case of minaprine synthesis, 3-chloro-6-methoxypyridazine is used as a starting material and is lithiated using lithium 2,2,6,6-tetramethylpiperidide. This process contributes to the development of minaprine, a compound with potential applications in the medical field.
Overall, 3-chloro-6-methoxypyridazine plays a significant role in the pharmaceutical industry, particularly in the synthesis of various compounds with potential therapeutic applications. Its unique chemical properties and reactivity make it a valuable compound for research and development in drug discovery.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 1466, 1995 DOI: 10.1021/jo00110a059

InChI:InChI=1/C5H5ClN2O/c1-9-5-3-2-4(6)7-8-5/h2-3H,1H3

Upstream product

• 67-56-1 methanol 
• 17284-97-8 3-Chloro-6-hydrazinopyridazine 
• 19064-65-4 3-methoxypyridazine 
• 935-04-6 benzyl vinyl ether 
• 75-20-7 calcium carbide 
• 141-30-0 3,6-dichlorpyridazine 
• 3315-60-4 methanolate 
• 23200-93-3 3-methoxypyridazine 1-oxide 
• 67-66-3 chloroform 
• 124-41-4 sodium methylate 

Downstream Products

• 99984-71-1 3-methoxy-6-phenoxy-pyridazine 
• 99984-42-6 6-methoxy-3-(phenylsulfanyl)pyridazine 
• 14634-52-7 6-Chlor-3-methoxy-pyridazin-1-oxid 
• 19064-65-4 3-methoxypyridazine 
• 153306-95-7 6-chloro-3-methoxy-α-phenylpyridazine-4-methanol 
• 68321-53-9 3-(phenylethynyl)-6-methoxypyridazine 
• 89466-36-4 3-chloro-6-methoxy-4-methylpyridazine 
• 89466-38-6 6-chloro-3-methoxy-4-methylpyridazine 
• 4578-42-1 3-methoxy-6-phenylpyridazine 
• 10330-56-0 3-Methoxy-6-(4-methylphenyl)pyridazine 
• 70751-01-8 3-Methoxy-6-(4-chlorophenyl)pyridazine 
• 242802-84-2 3-methoxy-6-(4-methoxyphenyl)pyridazine 
• 24049-46-5 3,6-Di-(4-methoxyphenyl)pyridazine 
• 103-84-4 Acetanilid 

Relevant academic research and scientific papers

One-Pot and Two-Chamber Methodologies for Using Acetylene Surrogates in the Synthesis of Pyridazines and Their D-Labeled Derivatives

Acetylene surrogates are efficient tools in modern organic chemistry with largely unexplored potential in the construction of heterocyclic cores. Two novel synthetic paths to 3,6-disubstituted pyridazines were proposed using readily available acetylene surrogates through flexible C2 unit installation procedures in a common reaction space mode (one-pot) and distributed reaction space mode (two-chamber): (1) an interaction of 1,2,4,5-tetrazine and its acceptor-functionalized derivatives with a CaC2?H2O mixture performed in a two-chamber reactor led to the corresponding pyridazines in quantitative yields; (2) [4+2] cycloaddition of 1,2,4,5-tetrazines to benzyl vinyl ether can be considered a universal synthetic path to a wide range of pyridazines. Replacing water with D2O and vinyl ether with its trideuterated analog in the developed procedures, a range of 4,5-dideuteropyridazines of 95–99% deuteration degree was synthesized for the first time. Quantum chemical modeling allowed to quantify the substituent effect in both synthetic pathways.

Pharmacological Evaluation of Novel Bioisosteres of an Adamantanyl Benzamide P2X7 Receptor Antagonist

Adamantanyl benzamide 1 was identified as a potent P2X7R antagonist but failed to progress further due to poor metabolic stability. We describe the synthesis and SAR of a series of bioisosteres of benzamide 1 to explore improvements in the pharmacological properties of this lead. Initial efforts investigated a series of heteroaromatic bioisosteres, which demonstrated improved physicochemical properties but reduced P2X7R antagonism. Installation of bioisosteric fluorine on the adamantane bridgeheads was well tolerated and led to a series of bioisosteres with improved physicochemical properties and metabolic stability. Trifluorinated benzamide 34 demonstrated optimal physicochemical parameters, superior metabolic stability (ten times longer than lead benzamide 1), and an improved physicokinetic profile and proved effective in the presence of several known P2X7R polymorphisms.

Microwave-enhanced efficient synthesis of some polyfunctional pyridazines

Microwave-enhanced highly efficient protocol for the synthesis of polyfunctional pyridazines beginning from 3,6-dichloropyridazine in environmentally benign ionic liquids have been developed. The products obtained were 3-amino-6-chloropyridazine, 3,6-diaminopyridazine, and 3-chloro-6- methoxypyridazine. These derivatives were then be converted to a variety of polyfunctional pyridazine derivatives. The ionic liquids used were 1-n-butyl-3-methylimidazolium hydroxide/tetrafluoroborate/hexafluorophosphate and 1,3-di-n-butylimidazolium hydroxide. This powerful strategy is less time-consuming green methodology. The ionic liquid employed may be recovered and recycled.

PYRROLIDINES AS NK3 RECEPTOR ANTAGONISTS

The present invention relates to a compounds of formula I wherein R1, R2, Ar1, Ar2, R′, R″, m, n, and o are defined in the specification or to a pharmaceutically active salt, racemic mixture, enantiomer, optical isomer or to tautomeric form thereof. The present compounds are high potential NK-3 receptor antagonists for the treatment of depression, pain, psychosis, Parkinson''s disease, schizophrenia, anxiety and attention deficit hyperactivity disorder (ADHD).

2-ARYLBENZOTHIOPHENE DERIVATIVES OR PHARCEUTICALLY ACCEPTABLE SALTS THEREOF, PREPARATION METHOD THEREOF, AND PHARCEUTICAL COMPOSITION FOR THE DIAGNOSIS OR TREATMENT OF DEGENERATIVE BRAIN DISEASE CONTAINING THE SAME AS ACTIVE INGREDIENT

2-arylbenzothiophene derivatives or pharmaceutically acceptable salts thereof, a preparation method thereof, and a pharmaceutical composition for the diagnosis or treatment of degenerative brain disease containing the same as an active ingredient. Since the 2-arylbenzothiophene derivatives of Formula 1 have a relatively high binding affinity for β-amyloid, they can be used as diagnostic reagents for diagnosing Alzheimer's disease at an early stage by non-invasive techniques when they are labeled with radioisotopes: wherein R1-R4, V, W, X, Y and Z are as defined in the Detailed Descript of the specification. Further, when the pharmaceutical composition containing the 2-arylbenzothiophene derivative binds with a low-molecular weight β-amyloid peptide binding compound, generation of malignant high-molecular weight β-amyloid deposits is minimized. Accordingly, the pharmaceutical composition can be used as a therapeutic agent of degenerative brain disease such as Alzheimer's disease.

3-ARYL-5,6-DISUBSTITUTED PYRIDAZINES

The present invention provides compounds of Formula (I) or (II) salt form or prodrug thereof, wherein variables are defined herein, that are modulators of metalloproteases such as matrix metalloproteases (MMPs) and ADAMs. The compounds or compositions described herein can be used to treat diseases associated with metalloprotease activity including, for example, arthritis, cancer, cardiovascular disorders, skin disorders, inflammation or allergic conditions.

Metalation of bromodiazines. Diazines XL

The syntheses of 2-bromopyrazine, 2,4-dibromopyrimidines, and 3-bromo-6-phenylpyrazine were improved and their metalation with lithium alkylamides was studied.

Synthesis of some 3,6-disubstituted pyridazines

Some novel 3-halo-6-(4-substituted-phenoxy)pyridazines and 3,6-di-(4- substituted-phenoxy)pyridazines were synthesized from 3,6-dichloropyridazine or 3,6-diiodopyridazine. 3,6-Diiodopyridazine was prepared from 3,6- dichloropyridazine using hydriodic acid/iodine monochloride.