1256579-62-0

Basic information

• Product Name: 9-broMo-6,6-diMethyl-8-(4-Morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile
• Synonyms: 9-broMo-6,6-diMethyl-8-(4-Morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile
• CAS NO: 1256579-62-0
• Molecular Formula: C28H29BrN4O2
• Molecular Weight: 533.45946
• Mol File: 1256579-62-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 9-broMo-6,6-diMethyl-8-(4-Morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 9-broMo-6,6-diMethyl-8-(4-Morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile(1256579-62-0)
• EPA Substance Registry System: 9-broMo-6,6-diMethyl-8-(4-Morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile(1256579-62-0)

Safety Data

• Hazardous Substances Data: 1256579-62-0(Hazardous Substances Data)

Usage

General Description

9-bromo-6,6-dimethyl-8-(4-morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile is a complex chemical compound with a heterocyclic structure. It contains a benzocarbazole core with a bromine atom and a dimethyl substituent at specific positions. Additionally, it has a piperidinyl-morpholinyl substituent and a nitrile group attached to the benzocarbazole ring. 9-broMo-6,6-diMethyl-8-(4-Morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile may have potential applications in pharmaceutical research and organic synthesis due to its unique structure and functional groups. Its heterocyclic nature suggests that it may exhibit biological activity and could be a valuable target for medicinal chemistry studies. However, further research would be necessary to fully understand its properties and potential uses.

Upstream product

• 1256579-48-2 trifluoro-methane sulfonic acid 9-bromo-3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yl ester 
• 53617-35-9 4-(piperidin-4-yl)morpholine 
• 1256579-06-2 9-bromo-8-hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile 

Downstream Products

• 1256580-46-7 C⁽²⁴⁸⁾H₅₄₀₂ 
• 1256589-74-8 alectinib hydrochloride 

Relevant articles and documents

Design and synthesis of a highly selective, orally active and potent anaplastic lymphoma kinase inhibitor (CH5424802)

Anaplastic lymphoma kinase (ALK) receptor tyrosine kinase is considered an attractive therapeutic target for human cancers, especially non-small cell lung cancer (NSCLC). Our previous study revealed that 8,9-side-chains of 6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole scaffold crucially affected kinase selectivity, cellular activity, and metabolic stability. In this work, we optimized the side-chains and identified highly selective, orally active and potent ALK inhibitor CH5424802 (18a) as the clinical candidate.

Preparation method of alectinib

The invention discloses a preparation method of alectinib. The preparation method comprises the following steps of using 2-(4-bromo-3-hydroxyphenyl)ethyl acetate as a raw material; performing trifluoromethanesulfonic acid etherification with trifluoromethyl sulfonic anhydride, so as to obtain a trifluoromethanesulfonic acid etherification compound; performing substitution reaction with the other raw material, namely 4-(4-piperidyl)morpholine, so as to obtain 2-{4-bromo-3-[4-morpholine-4-yl]piperidine-1-yl]phenyl}ethyl acetate, then performing dimethylation reaction and hydrolysis reaction to obtain 2-{4-bromo-3-[4-morpholine-4-yl]piperidine-1-yl]phenyl}-2-methyl propionate to be subjected to condensation reaction with malonic acid mono-tert-butyl ester, so as to obtain the 4-{4-bromo-3-[4-morpholine-4-yl]piperidine-1-yl]phenyl}-4-methyl-3-oxopentanoate tert-butyl; utilizing a typical Fischer indole synthesis method, enabling carbonyl and phenylhydrazine to cyclize under the acid catalyzing action to form indole nuclear parent; finally, performing cyclizing reaction, boric acidifying and catalytic coupling reaction, so as to prepare the alectinib. The preparation method has the advantages that the design of route method is reasonable, the price of raw material is low, the obtaining is easy, and the reaction condition is easily and effectively controlled.

Method for preparing alectinib

The invention discloses a method for preparing alectinib. The method comprises the following steps: firstly, by taking 6-bromine-7-methoxy-3,4-dihydro-2-naphthalenone as a raw material, performing hydrolysis so as to obtain methoxyl, performing deprotection, further performing trifluoromethanesulfonic acid esterification reaction on trifluoromethanesulfonic anhydride so as to obtain a trifluoromethanesulfonie ester compound, performing bimethylation reaction, performing substitution reaction on 1,1-dimethyl-6-bromine-2-oxo-3,4-dihydro-7-trifluoromethanesulfonate and another raw material, namely 4-(4-piperidyl) morpholine, implementing a classical reaction Fisher indole synthesis method, performing cyclization on carbonyl and phenylhydrazine under acid catalysis so as to form indole parent nucleus, and finally performing oxidation reaction, boric acid formation and catalytic coupling reaction, thereby obtaining the alectinib. The method is simple to operate and relatively low in cost, is a green and environmental-friendly process method, and is applicable to industrial production.