877399-00-3

Basic information

• Product Name: (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine
• Synonyms: (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine;[5-Bromo-3-[(1R)-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-yl]amine;[5-Bromo-3-[[(R)-1-(2,6-dichloro-3-fluorophenyl)ethyl]oxy]pyridin-2-yl]amine;(R)-5-BroMo-3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylaMine;(R)-5-broMo-3-[1-(2,6-dichloro-3-fluoropehnyl)ethoxy]pyridin-2-aMine;InterMediate Ⅰof Crizotinib (R)-5-broMo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-aMine;2-PyridinaMine, 5-broMo-3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-;Crizotinib-H
• CAS NO: 877399-00-3
• Molecular Formula: C13H10BrCl2FN2O
• Molecular Weight: 380
• EINECS: 1308068-626-2
• Product Categories: intermediate
• Mol File: 877399-00-3.mol
• Article Data: 40

Chemical Properties

• Melting Point: 107.0 to 111.0 °C
• Boiling Point: 423.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.643
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 5.55±0.10(Predicted)
• CAS DataBase Reference: (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine(877399-00-3)
• EPA Substance Registry System: (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine(877399-00-3)

Safety Data

• Hazardous Substances Data: 877399-00-3(Hazardous Substances Data)

Usage

Description

(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine is a chiral, pale yellow solid compound with a complex molecular structure featuring a pyridine ring, a bromo substituent, and an ethoxy chain connected to a dichloro-fluorophenyl group. (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine is characterized by its stereochemistry, with the R-configuration playing a crucial role in its properties and potential applications.

Uses

Used in Pharmaceutical Industry:
(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine is used as a key intermediate in the synthesis of Crizotinib, an antineoplastic drug. Crizotinib is a tyrosine kinase inhibitor that targets anaplastic lymphoma kinase (ALK) and has been approved for the treatment of non-small cell lung cancer (NSCLC) patients with ALK rearrangements. (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine's unique structure allows it to interact with the kinase domain of ALK, thereby inhibiting its activity and reducing tumor growth.
As a chiral intermediate, (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine is essential for the production of enantiomerically pure Crizotinib, ensuring the desired therapeutic effects and minimizing potential side effects associated with the less active or unwanted enantiomer.

Upstream product

• 877397-65-4 (S)‐1‐(2,6-dichloro-3-fluorophenyl)ethanol 
• 15128-82-2 3-hydroxy-2-nitropyridine 
• 877397-70-1 (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine 
• 877397-71-2 (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-aminopyridine 
• 74115-13-2 5-bromopyridine-3-ol 
• 1394346-24-7 (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine 
• 35486-42-1 2-amino-3,5-dibromopyridine 
• 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 
• 39903-01-0 2-amino-3-hydroxy-5-bromopyridine 
• 756520-67-9 (±)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine 

Downstream Products

• 1613147-74-2 (R)-tert-butyl 5-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)isoindoline-2-carboxylate 
• 1613147-76-4 (R)-5-(2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-7-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine 
• 1613147-75-3 (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1,2,3,4-tetrahydroisoquinoline-7-yl)pyridin-2-amine 
• 1613147-78-6 (R)-5-(2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine 
• 1613147-83-3 (R)-5-(2-(tert-butoxycarbonyl)-8-fluoro-1,2,3,4-tetrahydroisoquinolin-6-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine 
• 1613147-79-7 3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(8-fluoro-1,2,3,4-tetrahydroisoquinolin-6-yl)pyridin-2-amine 
• 1613147-93-5 5-(2-(tert-butoxycarbonyl)-4-fluoro-1,2,3,4-tetrahydroisoquinolin-6-yl)-3-((R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine 
• 1613147-99-1 5-(2-(tert-butoxycarbonyl)-4-((tetrahydro-2H-pyran-2-yl)oxy)-1,2,3,4-tetrahydroisoquinolin-6-yl)-3-((R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine 
• 1613148-01-8 5-(2-(tert-butoxycarbonyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-3-((R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine 
• 1613148-03-0 (R)-N,N-bis(tert-butoxycarbonyl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)pyridin-2-amine 
• 1613148-02-9 3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)pyridin-2-amine 
• 1613148-05-2 (R)-N,N-bis(tert-butoxycarbonyl)-5-(6-(tert-butoxycarbonyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine 
• 1613148-04-1 (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)pyridin-2-amine 
• 1613148-07-4 (R)-N,N-bis(tert-butoxycarbonyl)-5-(6-(tert-butoxycarbonyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-3-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine 

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 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.