54893-54-8

Basic information

• Product Name: 6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 54893-54-8
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177
• Mol File: 54893-54-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 267.1°Cat760mmHg
• Flash Point: 78.4°C
• Appearance: /
• Density: 1.034g/cm³
• Vapor Pressure: 0.00831mmHg at 25°C
• Refractive Index: 1.535
• PKA: 8.55±0.20(Predicted)
• CAS DataBase Reference: 6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline(54893-54-8)
• EPA Substance Registry System: 6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline(54893-54-8)

Safety Data

• Hazardous Substances Data: 54893-54-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H15NO/c1-12-6-5-9-7-11(13-2)4-3-10(9)8-12/h3-4,7H,5-6,8H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 200396-68-5 6-(tetrahydropyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline 
• 74-88-4 methyl iodide 
• 7647-01-0 hydrogenchloride 
• 123438-43-7 6-methoxy-2-methyl-3,4-dihydro-isoquinolinium; iodide 
• 19924-43-7 3-methoxyphenylacetonitrile 
• 42923-77-3 6-methoxy-1,2,3,4-tetrahydro-isoquinoline 
• 485-80-3 S-adenosyl-L-methionine 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 110339-54-3 N-[2-(3-methoxy-phenyl)-ethyl]-formamide 
• 14446-29-8 6-Methoxy-3,4-dihydroisoquinoline 
• 216064-47-0 6-(tetrahydropyran-2-yloxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline 
• 216064-45-8 2-(trifluoroacetyl)-1,2,3,4-tetrahydro-6-isoquinolinol 
• 14446-24-3 6-hydroxy-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 14097-39-3 N-methyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Discovery of Diaminopyrimidine Carboxamide HPK1 Inhibitors as Preclinical Immunotherapy Tool Compounds

Hematopoietic progenitor kinase 1 (HPK1), a serine/threonine kinase, is a negative immune regulator of T cell receptor (TCR) and B cell signaling that is primarily expressed in hematopoietic cells. Accordingly, it has been reported that HPK1 loss-of-function in HPK1 kinase-dead syngeneic mouse models shows enhanced T cell signaling and cytokine production as well as tumor growth inhibition in vivo, supporting its value as an immunotherapeutic target. Herein, we present the structurally enabled discovery of novel, potent, and selective diaminopyrimidine carboxamide HPK1 inhibitors. The key discovery of a carboxamide moiety was essential for enhanced enzyme inhibitory potency and kinome selectivity as well as sustained elevation of cellular IL-2 production across a titration range in human peripheral blood mononuclear cells. The elucidation of structure-activity relationships using various pendant amino ring systems allowed for the identification of several small molecule type-I inhibitors with promising in vitro profiles.

Pd-catalyzed ortho-arylation of 3,4-dihydroisoquinolones via C-H bond activation: synthesis of 8-aryl-1,2,3,4-tetrahydroisoquinolines

An efficient route to synthesize biologically interesting 8-aryl-1,2,3,4-tetrahydroisoquinoline has been developed. It involves the Pd-catalyzed direct arylation of 3,4-dihydroisoquinolones via C-H bond activation with aryl iodides to afford a variety of 8-arylated cross-coupling products, which are subsequently reduced to 8-aryl-1,2,3,4-tetrahydroisoquinolines in good to excellent yields.

A novel solid support for derivatization and subsequent N-alkylation of secondary amines: Preparation of N-alkylated 5- and 6-alkoxy-1,2,3,4-tetrahydroisoquinolines via Mitsunobu reaction

A hydroxymethylated polystyrene resin has been converted to its vinylsulfonylethyl ether (1) by DBU catalyzed addition of the hydroxy groups to divinyl sulfone. The support obtained was used to convert 5- and 6-(tetrahydropyran-2-yloxy)-1,2,3,4-tetrahydroisoquinolines to a set of N-alkylated tetrahydroisoquinolines bearing various 5- and 6-alkoxy substituents (5a-m). The synthesis involved attachment of the starting material to the support by Michael addition, acid-catalyzed removal of the tetrahydropyranyl protection, Mitsunobu etherification, quaternarization with alkyl amines, and release in solution with diisopropylethylamine.