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

• 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 
• 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 

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.

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.

Preparation method for alectinib

The invention discloses a preparation method for alectinib. The preparation method comprises the following steps: with 2-{4-bromo-3[4-(morpholin-4-yl)piperidin-1-yl]phenyl}-2-methylethyl propionate as a raw material, carrying out a reduction reaction to reduce the raw material into aldehyde; then subjecting the prepared aldehyde and tert-butyl 2,2-dichloroacetate to an addition-rearrangement reaction; then subjecting obtained 3-chloro-4-{4-bromo-3-[4-(morpholin-4-yl)piperidin-1-yl]phenyl}-4-methyl-tert-butyl 2-oxovalerate to a substitution reaction; carrying out a cyclization reaction and a hydrolysis reaction on prepared 3-(3-cyanophenylamino)ethyl-4-{4-bromo-3-[4-(morpholin-4-yl)piperidin-1-yl]phenyl}-4-methyl-tert-butyl 2-oxovalerate; subjecting obtained 6-cyano-2-{2-[4-bromo-3-(4-(morpholin-4-yl)piperidin-1-yl)phenyl]prop-2-yl}-1H-indole-3-carboxylic acid to a cyclization reaction; and successively carrying out a boric acid reaction and a catalytic coupling reaction on obtained 9-bromo-6,6-dimethyl-8-[4-(morpholin-4-yl)piperidin-1-yl]-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-formonitrile so as to obtain alectinib. The method has the advantages of simple operation and low cost, and is a green environment-friendly process suitable for industrial production.