61487-25-0

Usage

Uses

Used in Pharmaceutical Industry:
(2-Amino-3-chlorophenyl)methanol is used as a key intermediate in the synthesis of CGRP-receptor antagonists for the treatment of migraines. Its structural features allow for the development of compounds that can effectively block the activity of the calcitonin gene-related peptide (CGRP) receptor, thereby providing relief from migraine symptoms.
Additionally, (2-Amino-3-chlorophenyl)methanol is used as a building block in the synthesis of PI3K inhibitors, which are important in the development of targeted cancer therapies. PI3K (phosphatidylinositol-3-kinase) is an enzyme that plays a crucial role in cell growth, survival, and metabolism. Inhibiting its activity can help control the proliferation of cancer cells and potentially lead to the development of new treatments for various types of cancer.

InChI:InChI=1/C7H8ClNO/c8-6-3-1-2-5(4-10)7(6)9/h1-3,10H,4,9H2

Upstream product

• 6388-47-2 2-amino-3-chlorobenzoic acid 
• 77820-58-7 methyl 3-chloroanthranilate 

Downstream Products

• 910297-65-3 3-chloro-2-(2-chloroacetamido)benzyl 2-chloroacetate 
• 1369551-17-6 N-(2-chloro-6-hydroxymethylphenyl)-2,2,2-trifluoroacetamide 
• 1242061-77-3 N-(6-chloro-2-formylphenyl)-4-methylbenzenesulfonamide 
• 397322-82-6 2-amino-3-chlorophenylformaldehyde 
• 1269261-75-7 2-(bromomethyl)-8-chloro-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydroquinoline 
• 1269261-57-5 N-(2-(but-3-en-1-yl)-6-chlorophenyl)-4-methylbenzenesulfonamide 
• 1252576-11-6 N-(2-chloro-6-(chloromethyl)phenyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Chiral Phosphoric-Acid-Catalyzed Cascade Prins Cyclization

Asymmetric Prins cyclization of in situ generated quinone methides and o-aminobenzaldehyde has been developed with chiral phosphoric acid as an efficient catalyst. This unconventional method provides a facile access to diverse functionalized trans-fused pyrano-/furo-tetrahydroquinoline derivatives in excellent yield and with excellent diastereo- and enantioselectivities (up to 99% yield and 99% ee). Mechanistic studies suggested that the three adjacent tertiary stereocenters were constructed through the sequential formation of C-O, C-C, and C-N bonds.

Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.

Enantioselective synthesis of tunable chiral pyridine-aminophosphine ligands and their applications in asymmetric hydrogenation

A small library of tunable chiral pyridine-aminophosphine ligands were enantioselectively synthesized based on chiral 2-(pyridin-2-yl)-substituted 1,2,3,4-tetrahydroquinoline scaffolds, which were obtained in high yields and with excellent enantioselectivities via ruthenium-catalyzed asymmetric hydrogenation of 2-(pyridin-2-yl)quinolines. The protocol features a wide substrate scope and mild reaction conditions, enabling scalable synthesis. These chiral P,N ligands were successfully applied in the Ir-catalyzed asymmetric hydrogenation of benchmark olefins and challenging seven-membered cyclic imines including benzazepines and benzodiazepines. Excellent enantio- and diastereoselectivity (up to 99% ee and >20:1 dr), and/or unprecedented chemoselectivity were obtained in the asymmetric hydrogenation of 2,4-diaryl-3H-benzo[b]azepines and 2,4-diaryl-3H-benzo[b][1,4]diazepines.

Pd(II)-catalyzed enantioselective intramolecular oxidative amination utilizing (+)-camphorsulfonic acid

An enantioselective Pd(II)-catalyzed intramolecular oxidative amination reaction was developed utilizing the commercially available chiral X-type ligand (1S)-(+)-camphorsulfonic acid. The Wacker-type cyclization produced chiral indoline products with enantioselectivies up to 45% ee. Electronic structure calculations employing density functional theory support a trans-aminopalladation mechanism.

HETEROCYCLIC COMPOUNDS AND THEIR USE AS INHIBITORS OF PI3K ACTIVITY

Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorde

Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.

Extended Benzamide Derivatives as Modulators of the EP2 Receptor

The present invention relates to extended benzamide derivatives of the general formula I, to processes for preparation thereof and to use thereof for production of pharmaceutical compositions for treatment of disorders and indications associated with the

PROCESS FOR PREPARING N-(2-CHLORO-6-METHYLPHENYL)-2-[[6-[4-(2-HYDROXYETHYL)-1-PIPERAZINYL]-2-METHYL-4-PYRIMIDINYL]AMINO] -5-THIAZOLECARBOXAMIDE AND RELATED METABOLITES THEREOF

The present invention is directed to process for the preparation of metabolites as well as the parent compound of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl] amino]-5-thiazolecarboxamide, the compound of formula (I).

CONSTRAINED COMPOUNDS AS CGRP-RECEPTOR ANTAGONISTS

The invention encompasses constrained bicyclic and tricyclic CGRP-receptor antagonists, methods for identifying them, pharmaceutical compositions comprising them, and methods for their use in therapy for treatment of migraine and other headaches, neurogenic vasodilation, neurogenic inflammation, thermal injury, circulatory shock, flushing associated with menopause, airway inflammatory diseases, such as asthma and chronic obstructive pulmonary disease (COPD), and other conditions the treatment of which can be effected by the antagonism of CGRP-receptors.

'N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamides metabolites

The present invention is directed to metabolites of ′N-(2-Chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide, the compound of formula (I), pharmaceutical compositions thereof, and to methods