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

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

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.

Novel synthesis method of crizotinib intermediate (by machine translation)

The invention relates to a synthesis method of an organic compound, in particular to a novel synthesis method of a crizotinib intermediate, which comprises the following steps: taking cheap and easily available 2,6 - dichloro -3 - fluoroacetophenone as a starting raw material and reducing the CBS system to obtain S-shaped chiral alcohol. , 2 - Aminopyridine is taken as a raw material and bromine is brominated to obtain 3,5 - dibromo -2 - aminopyridine. The compound is condensed into an ether with a chiral alcohol under the action of an acid-binding agent to obtain the intermediate of the required configuration. The method is simple in reaction, short in route, less in three wastes, environment-friendly, high in yield of all steps, and less in raw material and reagent waste. (by machine translation)