111770-82-2

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 386, 1988 DOI: 10.1021/jo00237a029

Upstream product

• 624-28-2 2,5-dibromopyridine 
• 107-19-7 propargyl alcohol 
• 223463-13-6 2-iodo-5-bromopyridine 

Downstream Products

• 2859-68-9 3-(pyridin-2-yl)-propanol 
• 690266-80-9 3-[5-(4-chloro-phenyl)-pyridin-2-yl]-prop-2-yn-1-ol 

Relevant academic research and scientific papers

Catalytic Enantioselective Synthesis of Pyridyl Sulfoximines

With unique chemical and biological activity, sulfoximines have attracted enormous attention in the past decades, whereas limited reports exist for their synthesis via asymmetric catalysis. We report the synthesis of chiral sulfoximines through the desymmetrizing N-oxidation of pyridyl sulfoximines using an aspartic acid-containing peptide catalyst. Various mono- and bis-pyridyl sulfoximine oxides are obtained with up to 99:1 er. The directing group introduced on the substrate highly enhances the enantioinduction and could be easily removed to give the free N-H sulfoximines. Additionally, peptides with methyl ester and the methyl amide C-terminal protecting group give the opposite enantiomers of the product. A binding model is proposed to explain this phenomenon.

TRIAZOLE CARBAMATE PYRIDYL SULFONAMIDES AS LPA RECEPTOR ANTAGONISTS AND USES THEREOF

The present disclosure relates generally to compounds of Formula (I) that bind to Lysophosphatidic Acid Receptor 1 (LPAR1) and act as antagonists of LPAR1. The disclosure further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of LPAR1, including fibrosis and liver diseases such as non-alcoholic steatohepatitis (NASH).

LPA RECEPTOR ANTAGONISTS AND USES THEREOF

The present disclosure relates generally to compounds that bind to Lysophosphatidic Acid Receptor 1 (LPAR1) and act as antagonists of LPAR1. The disclosure further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of LPAR1, including fibrosis and liver diseases such as non-alcoholic steatohepatitis (NASH), interstitial lung disease (ILD), or chronic kidney disease (CKD).

Modular Syntheses of Phenanthroindolizidine Natural Products

A highly concise strategy for the total synthesis of phenanthroindolizidines was developed. The one-pot iterative Suzuki-Miyaura reaction of aryl boronic acids with ortho-bromoaryl N-methyliminodiacetate (MIDA) boronate followed by a second Suzuki-Miyaura reaction with a suitable pyridyl bromide provided ortho-aza-terphenyls. Subsequent saturation of the triple bond, treatment with mesyl chloride, and reduction of the resulting dihydroindolizidinium ring afforded the hexahydroindolizines. A final vanadium-catalyzed oxidative electrocyclization provided the desired alkaloids in only three column-separation operations.

TRIAZOLE N-LINKED CARBAMOYL CYCLOHEXYL ACIDS AS LPA ANTAGONISTS

The present invention provides compounds of Formula (I): or a stereoisomer, tautomer, or pharmaceutically acceptable salt or solvate thereof, wherein all the variables are as defined herein. These compounds are selective LPA receptor inhibitors.

CARBAMOYLOXYMETHYL TRIAZOLE CYCLOHEXYL ACIDS AS LPA ANTAGONISTS

The present invention provides compounds of Formula (I): or stereoisomers, tautomers, pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein all the variables are as defined herein. These compounds are selective LPA receptor inhibitors.

Palladium-catalyzed highly regioselective 2-alkynylation of 2,x-dihalopyridines Dedicated to Academician Xikui Jiang on the occasion of his 90th birthday and Professor Zhenchu Chen on the occasion of his 80th birthday

2,4-Dibromopyridines reacted with arylacetylenes, catalyzed by Pd(CF3COO)2/CuI/PPh3 in the presence of i-Pr2NH in CH3CN at reflux for 24 h, to afford 2-alkynylpyridines in good to high yields, while 2,3- and 2,5-dihalopyridines reacted with arylacetylenes, catalyzed by Pd(OAc)2/CuI/PPh3 in the presence of i-Pr2NH in CH3CN at reflux for 24 h, to afford 2-alkynylpyridines in good to high yields.

Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds

Alkyne compounds of formula I wherein A, B, W, X, Y, Z, R1, and R2 have the meanings given herein, which have MCH-receptor antagonistic activity and are useful for preparing pharmaceutical compositions for the treatment of metabolic disorders and/or eating disorders, particularly obesity and diabetes.

NOVEL ALKYNE COMPOUNDS HAVING AN MCH-ANTAGONISTIC EFFECT, AND MEDICAMENTS CONTAINING SAID COMPOUNDS

The invention relates to alkyne compounds of general formula (I), wherein the groups and radicals A, B, W, X, Y, Z, R1, and R2 have the meanings indicated in claim 1. The invention further relates to medicaments containing at least one inventive alkyne. The disclosed medicaments are suitable for the treatment of metabolic disorders and/or eating disorders, particularly adiposity and diabetes, as a result of the MCH receptor antagonistic activity thereof.

Methods for the synthesis of 5,6,7,8-tetrahydro-1,8-naphthyridine fragments for αvβ3 integrin antagonists

The preparation of 3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propan-1- amine 2a and 3-[(7R)-7-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl]propan-1- amine 2b, key intermediates in the synthesis of αvβ 3 antagonists, is described. The syntheses rely on the efficient double Sonogashira reactions of 2,5-dibromopyridine 3 with acetylenic alcohols 4a/4b and protected propargylamines 10a-e followed by Chichibabin cyclizations of 3,3′-pyridine-2,5-diyldipropan-1-amines 9a/9b.