24016-03-3

Basic information

• Product Name: 2-Amino-3-benzyloxypyridine
• Synonyms: TIMTEC-BB SBB000394;3-(BENZYLOXY)PYRIDIN-2-AMINE;3-Benzyloxy-2-pyridylamine;2-AMINO-3-BENZYLOXYPYRIDINE;3-Benzyloxy-2-aminopyridine;3-Benzyloxy-pyridin-2-ylamine;4-(Benzyloxy)-2-pyridinamine;Pyridine, 2-amino-3-(benzyloxy)-
• CAS NO: 24016-03-3
• Molecular Formula: C₁₂H₁₂N₂O
• Molecular Weight: 200.24
• EINECS: 245-983-9
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Heterocyclic Series;Pyridine;Pyridines derivates;Nucleotides and Nucleosides;Pyridines;Bases & Related Reagents;Nucleotides;C9 to C46;Heterocyclic Building Blocks;Amines;Aromatics;Heterocycles;A-AM;Bioactive Small Molecules;Building Blocks;C12;Cell Biology;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 24016-03-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 92-94 °C(lit.)
• Boiling Point: 337.96°C (rough estimate)
• Flash Point: 172.6 °C
• Appearance: Green to brown/Crystalline Powder
• Density: 1.1131 (rough estimate)
• Vapor Pressure: 2.02E-05mmHg at 25°C
• Refractive Index: 1.6660 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.40±0.10(Predicted)
• BRN: 392674
• CAS DataBase Reference: 2-Amino-3-benzyloxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3-benzyloxypyridine(24016-03-3)
• EPA Substance Registry System: 2-Amino-3-benzyloxypyridine(24016-03-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-24/25-36/37/39-22,26-36
• RIDADR: UN2811
• WGK Germany: 3
• Hazardous Substances Data: 24016-03-3(Hazardous Substances Data)

Usage

Description

2-Amino-3-benzyloxypyridine is an organic compound characterized by its brown crystalline powder form. It is a key intermediate in the synthesis of various pharmaceutical compounds, particularly those targeting Raf kinase, which plays a significant role in cell signaling and is associated with several diseases, including cancer.

Uses

Used in Pharmaceutical Industry:
2-Amino-3-benzyloxypyridine is used as a key intermediate in the preparation of pyridinyl/pyridazinyloxymethyl substituted Raf kinase inhibitors. These inhibitors are crucial in the development of targeted therapies for various diseases, including cancer, due to their ability to modulate the activity of Raf kinase.
Additionally, 2-Amino-3-benzyloxypyridine is used in the synthesis of 1-acetyl-2-[2-(3-benzyloxypyridinyl)]iminoimidazolidine, which is another important compound in the pharmaceutical industry. 2-Amino-3-benzyloxypyridine has potential applications in the development of new drugs targeting various diseases.
Furthermore, 2-Amino-3-benzyloxypyridine is utilized in the formation of 9-benzyloxy-3-ethoxycarbonylpyrido[1,2-a]pyrimidin-4-one upon condensation with diethyl ethoxymethylene malonate. 2-Amino-3-benzyloxypyridine serves as a building block for the development of novel therapeutic agents with potential applications in the treatment of various medical conditions.

Biochem/physiol Actions

2-Amino-3-benzyloxypyridine is an inhibitor of mitogen-activated protein kinase p38α activity.

InChI:InChI=1/C12H12N2O/c13-12-11(7-4-8-14-12)15-9-10-5-2-1-3-6-10/h1-8H,9H2,(H2,13,14)/p+1

Upstream product

• 16867-03-1 2-amino-3-hydroxypyridine 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 123420-42-8 isopropylidene N-(3-benzyloxy-2-pyridyl) aminomethylenemalonate 
• 151410-81-0 N-(3-(Benzyloxy)-2-pyridyl)phenylacetamidine 
• 107230-09-1 8-benzyloxy-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine 
• 96428-16-9 8-(phenylmethoxy)imidazo[1,2-a]pyridine 
• 94704-14-0 5-(8-Benzyloxy-3-methylimidazo[1,2-a]pyridin-2-yl)-2-benzoxazolinone 
• 936246-98-9 1-benzoyl-3-(3-(benzyloxy)pyridin-2-yl)thiourea 
• 1008796-22-2 9-(benzyloxy)-3-(2-hydroxyethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 

Relevant articles and documents

Highly Selective, Reversible Inhibitor Identified by Comparative Chemoproteomics Modulates Diacylglycerol Lipase Activity in Neurons

Diacylglycerol lipase (DAGL)-α and -β are enzymes responsible for the biosynthesis of the endocannabinoid 2-arachidonoylglycerol (2-AG). Selective and reversible inhibitors are required to study the function of DAGLs in neuronal cells in an acute and temporal fashion, but they are currently lacking. Here, we describe the identification of a highly selective DAGL inhibitor using structure-guided and a chemoproteomics strategy to characterize the selectivity of the inhibitor in complex proteomes. Key to the success of this approach is the use of comparative and competitive activity-based proteome profiling (ABPP), in which broad-spectrum and tailor-made activity-based probes are combined to report on the inhibition of a protein family in its native environment. Competitive ABPP with broad-spectrum fluorophosphonate-based probes and specific β-lactone-based probes led to the discovery of α-ketoheterocycle LEI105 as a potent, highly selective, and reversible dual DAGL-α/DAGL-β inhibitor. LEI105 did not affect other enzymes involved in endocannabinoid metabolism including abhydrolase domain-containing protein 6, abhydrolase domain-containing protein 12, monoacylglycerol lipase, and fatty acid amide hydrolase and did not display affinity for the cannabinoid CB1 receptor. Targeted lipidomics revealed that LEI105 concentration-dependently reduced 2-AG levels, but not anandamide levels, in Neuro2A cells. We show that cannabinoid CB1-receptor-mediated short-term synaptic plasticity in a mouse hippocampal slice model can be reduced by LEI105. Thus, we have developed a highly selective DAGL inhibitor and provide new pharmacological evidence to support the hypothesis that "on demand biosynthesis" of 2-AG is responsible for retrograde signaling.

Preparation method of high-purity paliperidone intermediate

The invention belongs to the technical field of medicine, and particularly discloses a preparation method of a high-purity paliperidone intermediate 3-(2-chloroethyl)-9-hydroxyl-2-methyl-6,7,8,9-tetrahydro-4H-pyridino[1,2-a] pyrimidine-4-ketone. The preparation method particularly comprises the following steps: preparing 9-(benzyloxy)-3-(2-chloroethyl)-2-methyl-4H-pyridino[1,2-a] pyrimidine-4-ketone by taking 2-amino-3-hydroxypyridine as a starting raw material and through benzyl protection, ring closure of alpha-acetyl-gamma-butyrolactone and chloro-substitution; dissolving the 9-(benzyloxy)-3-(2-chloroethyl)-2-methyl-4H-pyridino[1,2-a] pyrimidine-4-ketone into an alcohol solvent, adding acid and a palladium-charcoal catalyst, controlling hydrogen pressure, and after the reaction is completed, performing processes of filtering, concentrating, adjusting the pH value, extracting, concentrating and refining to obtain white-like powdered 3-(2-chloroethyl)-9-hydroxyl-2-methyl-6,7,8,9-tetrahydro-4H-pyridino[1,2-a] pyrimidine-4-ketone. The preparation method is short in cycle, the product is white-like, the yield reaches 70 percent or higher, the purity reaches 99 percent or higher, related impurities of chlorine-removed byproducts are avoided, and the preparation method is suitable for industrialized enlarged production.

COMPOUND, COMPOSITIONS, AND METHODS

Compounds having activity as LRRK2 inhibitors are disclosed. The compounds are of formula (I) including stereoisomers, tautomers, pharmaceutically acceptable salts and prodrugs thereof. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.