877397-71-2

Basic information

• Product Name: (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine
• Synonyms: (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine;3-[[(1R)-1-(2,6-Dichloro-3-fluorophenyl)ethyl]oxy]pyridin-2-amine;2-Pyridinamine, 3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-
• CAS NO: 877397-71-2
• Molecular Formula: C13H11Cl2FN2O
• Molecular Weight: 301
• Mol File: 877397-71-2.mol

Chemical Properties

• Appearance: /
• Density: 1.400
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine(877397-71-2)
• EPA Substance Registry System: (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine(877397-71-2)

Safety Data

• Hazardous Substances Data: 877397-71-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-(1,(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine is used as a potential drug candidate for various therapeutic applications due to its unique chemical structure and properties. Its amine and fluorophenyl groups may offer specific binding affinities and interactions with biological targets, making it a promising candidate for the development of new medications.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine serves as a valuable compound for studying the structure-activity relationships of drug molecules. Its synthesis and modification can provide insights into the design of more effective and selective pharmaceutical agents, contributing to the advancement of drug discovery and development processes.

Upstream product

• 877397-70-1 (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine 
• 877397-65-4 (S)‐1‐(2,6-dichloro-3-fluorophenyl)ethanol 
• 15128-82-2 3-hydroxy-2-nitropyridine 
• 330156-50-8 (R)-1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol 
• 54231-35-5 3-fuoro-2-nitropyridine 
• 290835-85-7 2',6'-dichloro-3'-fluoroacetophenone 
• 877399-98-9 C₉H₉Cl₂FO₃S 
• 756520-66-8 1-(2,6-dichloro-3-fluorophenyl)ethanol 
• 1229457-91-3 1-(2,6-dichloro-3-fluorophenyl)ethyl methanesulfonate 
• 756521-08-1 (±)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine 

Downstream Products

• 1613148-19-8 3-((R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)pyridin-2-amine 
• 1448326-33-7 (S)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-aminopyridine 

Relevant articles and documents

Preparation method of deuterated crizotinib and derivatives thereof

The invention relates to a preparation method of deuterated crizotinib and derivatives thereof, and belongs to the technical field of synthesis of medical compounds. Four deuterated crizotinib with different configurations are synthesized, the influence of the deuterated position and different chirality of the deuterated crizotinib on the biological activity and the drug metabolism property of thecrizotinib is investigated, and the result shows that the deuterated crizotinib and the crizotinib have similar anti-cancer activity. Compared with a deuterated crizotinib raceme and crizotinib, thedeuterated crizotinib has certain physicochemical property advantages, has good anticancer application prospects, and provides a new compound for synthesis of novel antitumor drugs. The resolution ofthe racemate phenylethanol derivative is a key step for synthesizing the deuterated crizotinib, the ee value of the racemate phenylethanol derivative directly influences the ee value of a final product, and the resolution method has the characteristics of easiness in operation, low cost and the like.

Novel pyridine derivatives having inhibition activity against SHIP2 and pharmaceutical compositions with the components

The present invention relates to a use as a pyridine derivative and/or a SHIP2 inhibitor. More specifically, the present invention relates to: a pyridine derivative of chemical formula I or pharmaceutically acceptable salt thereof; a method for manufacturing compounds thereof; and a pharmaceutical composition containing the compounds as active components. The pyridine derivative and the pharmaceutically acceptable salt thereof are useful as therapeutic agents for diseases related to SHIP2, such as Alzheimerandprime;s dementia, hypertension, cancer, diabetes, etc.COPYRIGHT KIPO 2020

Novel pyridine derivatives having inhibition activity against SHIP2 and pharmaceutical compositions with the components

The present invention relates to a pyridine derivative and/or a use as a SHIP2 inhibitor. The present invention relates to a pyridine derivative of chemical formula I or a pharmaceutically acceptable salt thereof, a method for preparing the compounds, and a pharmaceutical composition containing the compounds as an active ingredient. The pyridine derivative and pharmaceutically acceptable salt thereof is useful as drugs for the treatment of diseases related to SHIP2, such as Alzheimerandprime;s dementia, hypertension, cancer, and diabetes.COPYRIGHT KIPO 2021

Synthesis of a Crizotinib Intermediate via Highly Efficient Catalytic Hydrogenation in Continuous Flow

Kilogram-scale highly selective catalytic hydrogenation of the aryl nitro group in the intermediate of crizotinib has been developed, which adopted continuous-flow technology with prepassivated Raney Ni as a catalyst at room temperature. According to the reaction condition optimization, side reactions such as dehalogenation, debenzylation, and reduction of other unsaturated functional groups were inhibited eminently. Moreover, catalytic hydrogenation of (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine (compound I) afforded the desired product (R)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-amine (compound II) with high selectivity (99.9%) and high conversion (99.5%). Finally, high-quality crizotinib was synthesized from intermediate II.

Discovery of 2-aminopyridines bearing a pyridone moiety as potent ALK inhibitors to overcome the crizotinib-resistant mutants

Despite the initial benefit demonstrated in clinical setting with ALK inhibitors, the challenging resistant mutants (F1174L, L1196M and G1202R) invariably developed. In this work, a series of 2-aminopyridine derivatives were designed and synthesized by C-5 position incorporation of a 2-pyridone moiety and bioisosteric replacement of the C-3 position linkers. Optimization of the 2-aminopyridine derivatives led to the identification of hit 18d displaying a significant growth inhibition against a variety of ALK-addicted cancer cells. Especially in the case of ALK-positive Karpas-299 cell, 18d exhibited excellent anti-proliferative potency with an IC50 value of about 40 nM. Moreover, 18d demonstrated encouraging activities against wild-type ALK (19 nM), ROS1 (2.3 nM) as well as challenging crizotinib-resistant ALKL1196M and ALKG1202R mutants with IC50 values of 45 nM and 22 nM, respectively. Additionally flow cytometric analysis indicates that 18d inhibited Karpas-299 cell viability via G1 phase arrest. Taken together, this work provided a promising ALK inhibitor to circumvent the clinical crizotinib-resistant mutants.

A micro-channel reactor synthesis [...] intermediates (by machine translation)

The present invention discloses a micro-channel reactor synthesis [...] intermediates, which belongs to the organic synthesis in the technical field of anticancer drug synthesis. The method is that the 3 - (1 - (2, 6 - dichloro - 3 - fluorophenyl) ethoxy)

PYRIDINE SUBSTITUTED 2-AMINOPYRIDINE PROTEIN KINASE INHIBITOR CRYSTAL

The present invention discloses a crystal of citrate salt of pyridine-substituted 2-aminopyridine-based protein kinase inhibitors, in particular, to crystal of 5-((R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-4′-methoxy-6′-((S)-2-methylpiperazin-1-yl)-3,3′-bipyridin-6-amine citrate salt, a method for preparation thereof, a crystalline composition and a pharmaceutical composition comprising the crystal, and further discloses the use of crystals of citrate salt of the compound of Formula I in protein kinase-related diseases. The crystals of citrate salt according to the present invention are superior to 5-((R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-4′-methoxy-6′-((S)-2-methylpiperazin-1-yl)-3,3′-bipyridin-6-amine or other salts of 5-((R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-4′-methoxy-6′-((S)-2-methylpiperazin-1-yl)-3,3′-bipyridin-6-amine in at least one aspect of bioavailability, hygroscopicity, stability, solubility, purity, ease of preparation, and the like.

Crizotinib intermediate, preparation method and crizotinib preparation method

The invention relates to a crizotinib intermediate, a preparation method and a crizotinib preparation method, in particular to an intermediate of crizotinib which has the structure of a formula (CZT-5) as shown in the description and the structure of a formula (CZT-9) as shown in the description, a preparation method of the intermediate and a preparation method of a crizotinib with the structure of a formula (CZT-11). The method provided by the invention has the characteristics of short route, high yield, easiness in acquisition of raw materials, high reaction selectivity and the like, chiral resolution is not required in a synthetic process, the utilization rate of the raw materials is increased, the path costs are low, and therefore, the method can meet requirements of large-scale industrial production.

Preparation method of crizotinib intermediate

The invention discloses a synthetic method of anti-tumor molecular targeted drug crizotinib, belongs to the field of pharmaceuticals, and relates to a synthetic method of a crizotinib intermediate. The method comprises two reduction processes: a bromination reaction process comprises the following reaction steps: a reduction process I: carrying out reduction reaction on a (R)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxyl]-2-nitropyridine compound and sodium dithionate under a mechanical chemical condition to generate (R)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxyl]-2-aminopyridine; a reduction process II: dissolving the (R)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxyl]-2-nitropyridine compound into an organic solvent, carrying out catalytic hydrogenation and reduction treatment to generate (R)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxyl]-2-aminopyridine; the bromination reaction process comprises a step of carrying out reaction between the compound and potassium hydrogen persulfate as well as bromate to obtain the crizotinib intermediate. The process is low in cost, the raw materials are easy to purchase, the operation is simple, convenient and safe, and the yield is high; moreover, the process is suitable for large-scale production.

Substituted ring compound and its method and use thereof

The invention provides a substituted cyclic compound as well as a use method and application thereof. The compound is a compound as shown in a formula (I) or stereoisomers, stereomers, tautomers, nitric oxides, solvates, metabolites and pharmaceutically acceptable salts or prodrugs of the compound as shown in the formula (I). The invention further provides a medicament composition containing the compound. The compound and the medicament composition are capable of regulating the activity of protein kinase in a biological sample body and are used for protecting, treating or relieving proliferative diseases of patients. The formula (I) is as shown in the specification.