65361-26-4

Usage

Uses

Used in Organic Synthesis:
Benzo[b]thiophene-2-carbonyl chloride, 4,5,6,7-tetrahydro(9CI) is used as a synthetic intermediate for the creation of various organic molecules. Its unique structure allows for the introduction of the benzo[b]thiophene-2-carbonyl chloride functional group, which can be key in the synthesis of complex organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, Benzo[b]thiophene-2-carbonyl chloride, 4,5,6,7-tetrahydro(9CI) serves as a valuable building block for the development of new drugs. Its tetrahydro structure and carbonyl chloride group can be incorporated into the molecular frameworks of potential therapeutic agents, contributing to the discovery of novel pharmaceuticals.
Used in Heterocyclic Compound Synthesis:
Benzo[b]thiophene-2-carbonyl chloride, 4,5,6,7-tetrahydro(9CI) is also used as a key component in the synthesis of heterocyclic compounds. Its tetrahydro structure makes it a versatile building block for the creation of diverse heterocyclic systems, which are prevalent in many biologically active molecules and pharmaceuticals.

Upstream product

• 40133-07-1 4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic acid 
• 19282-45-2 ethyl 4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylate 
• 13129-17-4 4,5,6,7-tetrahydrobenzo[b]thiophene 

Downstream Products

• 910235-71-1 N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamide 
• 910232-80-3 4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid [3-(6-{3-amino-4-[(2-hydroxy-ethyl)-methyl-carbamoyl]-phenylamino}-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl)-2-methyl-phenyl]-amide 
• 910235-74-4 4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid [3-(6-{4-[(2-hydroxy-ethyl)-methyl-carbamoyl]-3-nitro-phenylamino}-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl)-2-methyl-phenyl]-amide 
• 1433824-11-3 {4-fluoro-2-[6-({4-[4-(oxetan-3-yl)piperazin-1-yl]phenyl}amino)-9-{[2-(trimethylsilyl)ethoxy]methyl}purin-2-yl]-6-{6-oxo-8-thia-5-azatricyclo[7.4.0.0^2,7]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-5-yl}phenyl}methyl acetate 
• 1346672-58-9 2-bromo-6-(1-oxo-3,4,5,6,7,8-hexahydrobenzothieno[2,3-c]pyridin-2(1H)-yl)benzyl acetate 
• 1346672-54-5 5,6,7,8-tetrahydro-1H-benzo[b]cyclopenta[d]thiophen-3(2H)-one 
• 1346671-16-6 5-{3-[5-({5-[2-(dimethylamino)ethoxy]pyridin-2-yl}amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl]-5-fluoro-2-(hydroxymethyl)phenyl}-8-thia-5-azatricyclo[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-6-one 
• 1346675-77-1 {2-[5-({5-[2-(dimethylamino)ethoxy]pyridin-2-yl}amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl]-4-fluoro-6-{6-oxo-8-thia-5-azatricyclo[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-5-yl}phenyl}methyl acetate 
• 1346670-48-1 5-[5-fluoro-2-(hydroxymethyl)-3-[1-methyl-5-({5-[(1-methylazetidin-3-yl)oxy]pyridin-2-yl}amino)-6-oxo-1,6-dihydropyridin-3-yl]phenyl]-8-thia-5-azatricyclo[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-6-one 
• 1346674-75-6 {4-fluoro-2-[1-methyl-5-({5-[(1-methylazetidin-3-yl)oxy]pyridin-2-yl}amino)-6-oxo-1,6-dihydropyridin-3-yl]-6-{6-oxo-8-thia-5azatricyclo[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-5-yl}phenyl}methyl acetate 
• 1346669-85-9 5-(3-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-5-fluoro-2-(hydroxymethyl)phenyl)-8-thia-5-azatricyclo-[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-6-one 
• 1346673-40-2 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-fluoro-6-(1-oxo-3,4,5,6,7,8-hexahydrobenzothieno[2,3-c]pyridin-2(1H)-yl)benzyl acetate 
• 1346673-39-9 (2-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxopyridin-3-yl}-4-fluoro-6-{6-oxo-8-thia-5-azatricyclo[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-5-yl}phenyl)methyl acetate 
• 1346669-71-3 5-[5-fluoro-2-(hydroxymethyl)-3-(4-methyl-6-{[4-(morpholin-4-yl)phenyl]amino}-5-oxo-4,5-dihydropyrazin-2-yl)phenyl]-8-thia-5-azatricyclo[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-6-one 

Relevant academic research and scientific papers

Pyrrolopyrimidine BTK inhibitor as well as preparation method and application thereof

The invention provides a pyrrolopyrimidine BTK inhibitor as well as a preparation method and application thereof, and belongs to the technical field of biological medicines. The compound has the structural general formula shown in a formula (I). In-flight

Enantioselective Synthesis of Five-Membered-Ring Atropisomers with a Chiral Rh(III) Complex

Axially chiral atropisomeric compounds are widely applied in asymmetric catalysis and medicinal chemistry, and efficient methods for their synthesis are in high demand. This applies in particular to atropisomers derived from five-membered aromatic rings because their lower barrier for rotation among the biaryl axis limits their asymmetric synthesis. We report here an enantioselective C-H functionalization method using our chiral RhJasCp complex for the synthesis of the biaryl atropisomer types that can be accessed from three different five-membered-ring heterocycles.

Discovery of N-(3-(5-((3-acrylamido-4-(morpholine-4-carbonyl)phenyl)amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4-(tert-butyl)benzamide (CHMFL-BTK-01) as a highly selective irreversible Bruton's tyrosine kinase (BTK) inhibitor

Currently there are several irreversible BTK inhibitors targeting Cys481 residue under preclinical or clinical development. However, most of these inhibitors also targeted other kinases such as BMX, JAK3, and EGFR that bear the highly similar active cysteine residues. Through a structure-based drug design approach, we discovered a highly potent (IC50: 7?nM) irreversible BTK inhibitor compound 9 (CHMFL-BTK-01), which displayed a high selectivity profile in KINOMEscan (S score (35)?=?0.00) among 468 kinases/mutants at the concentration of 1?μM. Compound 9 completely abolished BMX, JAK3 and EGFR's activity. Both X-ray crystal structure and cysteine-serine mutation mediated rescue experiment confirmed 9's irreversible binding mode. 9 also potently inhibited BTK Y223 auto-phosphorylation (EC50: 30?nM), arrested cell cycle in G0/G1 phase and induced apoptosis in U2932 and Pfeiffer cells. We believe these features would make 9 a good pharmacological tool to study the BTK related pathology.

Potent and selective Bruton's tyrosine kinase inhibitors: Discovery of GDC-0834

SAR studies focused on improving the pharmacokinetic (PK) properties of the previously reported potent and selective Btk inhibitor CGI-1746 (1) resulted in the clinical candidate GDC-0834 (2), which retained the potency and selectivity of CGI-1746, but wi

Ethyl 2-Aminothiophene-3-Carboxylates in the Synthesis of Isomeric Thienopyridines

A convenient method for the synthesis of thieno[3,2-c]pyridinones was developed. A number of thiophene derivatives was prepared, and the possibility of using thiophene desamino derivatives for the design of potentially biologically active molecules was demonstrated.

BICYCLIC PIPERAZINE COMPOUNDS

Bicyclic piperazine compounds of Formula I are provided, including stereoisomers, tautomers, and pharmaceutically acceptable salts thereof, useful for inhibiting Btk kinase, and for treating immune disorders such as inflammation mediated by Btk kinase. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, and treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

PYRIDONE AND AZA-PYRIDONE COMPOUNDS AND METHODS OF USE

Pyridone and aza-pyridone compounds of Formula I are provided, including stereoisomers, tautomers, and pharmaceutically acceptable salts thereof, useful for inhibiting Btk kinase, and for treating immune disorders such as inflammation mediated by Btk kinase. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, and treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

CERTAIN SUBSTITUTED AMIDES, METHOD OF MAKING, AND METHOD OF USE THEREOF

Compounds of Formula I that inhibit Btk are described herein. Pharmaceutical compositions comprising at least one compound of Formula I, together with at least one pharmaceutically acceptable vehicle chosen from carriers, adjuvants, and excipients, are de

KINASE INHIBITORS, AND METHODS OF USING AND IDENTIFYING KINASE INHIBITORS

Methods of inhibiting BTK activity by inhibiting phosphorylation of Y551 of BTK, methods of treating patients by inhibiting BTK activity by inhibiting phosphorylation of Y551 of BTK, chemical entities that bind to BTK and inhibited complexes are provided.

Structure-property relationships in mixed oligoheterocycles based on end-capped oligothiophenes

Novel mixed oligoheterocycles 1-5, containing thiophene/thiazole, thiophene/1,3,4-thiadiazole, thiophene/oxazole, or thiophene/1,3,4-oxadiazole moieties, were synthesized. The introduction of electronegative heteroatoms such as oxygen and nitrogen into the conjugated π-system leads to a more pronounced acceptor character than that found in the analogous oligothiophenes. Characterization of the redox properties reveals that the reduction of the mixed oligomers is facilitated while oxidation is shifted to higher potentials. For this series, clear structure-property relationships could be found by comparing optical properties, in particular absorptions, emissions and fluorescence quantum yields in solution. The X-ray structural determination of mixed thiophene/1,3,4-oxadiazole heptamer 5 indicates that the replacement of thiophene units by 1,3,4-oxadiazoles has a strong influence on the molecular arrangement and intermolecular interactions in the solid state.