123696-01-5

Basic information

• Product Name: 5-METHOXYPYRIDAZIN-3(2H)-ONE
• Synonyms: 5-METHOXYPYRIDAZIN-3(2H)-ONE;AURORA KA-3645;5-Methoxy-2,3-dihydropyridazin-3-one;3-hydroxy-5-Methoxypyridazine;-METHOXYPYRIDAZIN-3(2H)-ONE;3-methoxy-3(2H)-pyridazinone;3(2H)-Pyridazinone,5-methoxy-
• CAS NO: 123696-01-5
• Molecular Formula: C5H6N2O2
• Molecular Weight: 126.11
• EINECS: 200-001-2
• Mol File: 123696-01-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 148-150 °C
• Boiling Point: 363 °C at 760 mmHg
• Flash Point: 173.3 °C
• Appearance: /
• Density: 1.3 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.57±0.40(Predicted)
• CAS DataBase Reference: 5-METHOXYPYRIDAZIN-3(2H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXYPYRIDAZIN-3(2H)-ONE(123696-01-5)
• EPA Substance Registry System: 5-METHOXYPYRIDAZIN-3(2H)-ONE(123696-01-5)

Safety Data

• Hazardous Substances Data: 123696-01-5(Hazardous Substances Data)

Usage

General Description

5-Methoxypyridazin-3(2H)-one is a chemical compound with the molecular formula C5H6N2O2. It is a derivative of pyridazine and is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. 5-METHOXYPYRIDAZIN-3(2H)-ONE is known for its potent biological activities, including antimicrobial and antifungal properties. It is also used as a reagent in organic synthesis, particularly in the preparation of heterocyclic compounds. Its unique structure and reactivity make it a valuable tool for chemical research and drug discovery efforts.

Upstream product

• 63910-43-0 4-chloro-5-methoxypyridazin-3-(2H)-one 
• 152732-22-4 4-bromo-5-methoxypyridazin-3(2H)-one 
• 938045-16-0 2-((benzyloxy)methyl)-4-chloro-5-methoxypyridazin-3(2H)-one 
• 173206-12-7 4-chloro-5-methoxy-2-(tetrahydro-2H-pyran-2-yl)-3(2H)-pyridazinone 
• 173206-14-9 5-methoxy-2-(tetrahydro-2H-pyran-2-yl)-3(2H)-pyridazinone 

Downstream Products

• 17285-29-9 5-hydroxy-3(2H)-pyridazinone 
• 123696-02-6 3-chloro-5-methoxy-pyridazine 
• 20733-11-3 4-methoxypyridazine 
• 2096-20-0 3,5-dimethoxypyridazine 

Relevant articles and documents

A large scale synthesis of 3-chloro-5-methoxypyridazine

A large scale synthesis of 3-chloro-5-methoxypyridazine was developed (18 moles) that relies on the protection of the pyridazinone nitrogen of 4,5-dichloro-3(2H)-pyridazinone as the tetrahydropyranyl derivative 2. The 5-chloro position of the protected pyridazinone was selectively displaced with methoxide to give 3 followed by catalytic hydrogenation of the 4-chloro group to give 4. Removal of the protecting group with acid followed by phosphorous oxychloride treatment gave the target compound 6 in good yield. This route is superior to the previously described synthesis of this compound.

HETEROARYLBENZIMIDAZOLE COMPOUNDS

The present invention covers heteroarylbenzimidazole compounds of general formula (I) in which R1, R2, R3, R4 and R5 are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of hyperproliferative and/or inflammatory disorders, as a sole agent or in combination with other active ingredients.

N-phenyl-4-pyrazolo[1,5-6]pyridazin-3-ylpyrimidin-2-amines as potent and selective inhibitors of glycogen synthase kinase 3 with good cellular efficacy

Glycogen synthase kinase 3 regulates glycogen synthase, the rate-determining enzyme for glycogen synthesis. Liver and muscle glycogen synthesis is defective in type 2 diabetics, resulting in elevated plasma glucose levels. Inhibition of GSK-3 could potentially be an effective method to control plasma glucose levels in type 2 diabetics. Structure-activity studies on a N-phenyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine series have led to the identification of potent and selective compounds with good cellular efficacy. Molecular modeling studies have given insights into the mode of binding of these inhibitors. Since the initial leads were also potent inhibitors of CDK-2/CDK-4, an extensive SAR was performed at various positions of the pyrazolo[1,5-b] pyridazin core to afford potent GSK-3 inhibitors that were highly selective over CDK-2. In addition, these inhibitors also exhibited very good cell efficacy and functional response. A representative example was shown to have good oral exposure levels, extending their utility in an in vivo setting. These inhibitors provide a viable lead series in the discovery of new therapies for the treatment of type 2 diabetes.