100189-16-0

Basic information

• Product Name: 3-Pyridinemethanol,alpha,6-dimethyl-(6CI,9CI)
• Synonyms: 3-Pyridinemethanol,alpha,6-dimethyl-(6CI,9CI);3-Pyridinemethanol, a,6-dimethyl-;5-(1-Hydroxyethyl)-2-methylpyridine;1-(6-Methyl-3-pyridinyl)ethanol;a,6-diMethyl-3-PyridineMethanol;dl-2-Methyl-5-[1-hydroxyethyl]pyridine;α,6-DiMethyl-3-pyridineMethanol;3-(1-Hydroxyethyl)-6-Methylpyridine
• CAS NO: 100189-16-0
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.181
• EINECS: 125-856-9
• Product Categories: PYRIDINE;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 100189-16-0.mol

Chemical Properties

• Boiling Point: 246.655°C at 760 mmHg
• Flash Point: 102.974°C
• Appearance: /
• Density: 1.055g/cm³
• Vapor Pressure: 0.014mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 13.77±0.20(Predicted)
• CAS DataBase Reference: 3-Pyridinemethanol,alpha,6-dimethyl-(6CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinemethanol,alpha,6-dimethyl-(6CI,9CI)(100189-16-0)
• EPA Substance Registry System: 3-Pyridinemethanol,alpha,6-dimethyl-(6CI,9CI)(100189-16-0)

Safety Data

• Hazardous Substances Data: 100189-16-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Pyridinemethanol, alpha,6-dimethyl-(6CI,9CI) is used as an intermediate in the synthesis of various metabolites and pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with specific therapeutic properties.
Used in Synthesis of Pioglitazone Metabolites:
Specifically, 3-Pyridinemethanol, alpha,6-dimethyl-(6CI,9CI) is utilized in the synthesis of metabolites of the antidiabetic and antihyperglycemic agent Pioglitazone (P471000). This application highlights its importance in the development of treatments for diabetes and related conditions.

InChI:InChI=1/C8H11NO/c1-6-3-4-8(5-9-6)7(2)10/h3-5,7,10H,1-2H3

Upstream product

• 104-90-5 5-ethyl-2-methyl-pyridine 
• 36357-38-7 1-(6-methyl-pyridin-3-yl)-ethanone 
• 2024-89-7 5-ethyl-2-methyl-pyridine; hydrochloride 
• 140-76-1 2-methyl-5-vinylpyridine 
• 5470-70-2 Methyl 6-methylnicotinate 
• 21683-58-9 ethyl 3-(2-methyl-5-pyridinyl)-3-oxopropanoate 
• 75-16-1 methylmagnesium bromide 
• 544-97-8 dimethyl zinc(II) 

Downstream Products

• 146062-57-9 3-(1-(methoxymethoxy)ethyl)-6-methylpyridine 
• 36357-38-7 1-(6-methyl-pyridin-3-yl)-ethanone 
• 104-89-2 5-ethyl-2-methylpiperidine 
• 146062-44-4 Hydroxypioglitazone 
• 184766-25-4 4-{2-[5-(1-methoxymethoxy-ethyl)-pyridin-2-yl]-ethoxy}benzaldehyde 
• 184766-39-0 5-(4-(2-(5-(1-(methoxymethoxy)ethyl)pyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione 
• 146062-59-1 5-(1-methoxymethoxyethyl)-2-<2-(4-nitrophenoxy)ethyl>pyridine 
• 146062-45-5 Ketopioglitazone 
• 1026292-59-0 2-Imino-5-(4-{2-[5-(1-methoxymethoxy-ethyl)-pyridin-2-yl]-ethoxy}-benzyl)-thiazolidin-4-one 
• 146062-60-4 methyl 2-bromo-3-<4-<2-<5-(1-memthoxymethoxyethyl)-2-pyridyl>ethoxy>phenyl>propionate 

Relevant articles and documents

PROCESS FOR PREPARING 5-[[4-[2-[5-(1-HYDROXYETHYL)-2-PYRIDINYL]ETHOXY]PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE AND SALTS THEREOF

The disclosure provides a process of making the compound of Formula I, and pharmaceutically acceptable salts thereof: and the process of making the intermediate of Formula III: wherein PG is as defined as set forth in the specification.

NOVEL PYRIMIDINE CARBOXAMIDES AS INHIBITORS OF VANIN-1 ENZYME

Compounds, pharmaceutically acceptable salts thereof, are disclosed wherein the compounds have the structure of (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates a

2,4-THIAZOLIDINEDIONE DERIVATIVES IN THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS

The present invention provides 5-(4-(2-(5-(1-hydroxyethyl)pyridine-2-yl)ethoxy) benzyl)thiazolidine-2,4-dione and novel stereoisomers of said compound for use in the treatment of central nervous system (NS) disorders.

COMPOUNDS WHICH POTENTIATE THE AMPA RECEPTOR AND USES THEREOF IN MEDICINE

Compounds of formula (I) and salts thereof are provided: wherein n is 0, 1, 2 or 3; R1 is selected from phenyl and pyridyl, each of which is optionally substituted by one or two groups independently selected from C1-4alkyl and haloge

Synthesis and biological activity of metabolites of the antidiabetic, antihyperglycemic agent pioglitazone

Pioglitazone (5-(4-(2-(5-ethyl-2-pyridyl)ethoxy)benzyl)-2,4- thiazolidinedione, 2) is a prototypical antidiabetic thiazolidinedione that had been evaluated for possible clinical development. Metabolites 6-9 have been identified after dosing of rats and dogs. Ketone 10 has not yet been identified as a metabolite but has been added to the list as a putative metabolite by analogy to alcohol 6 and ketone 7. We have developed improved syntheses of pioglitazone (2) metabolites 6-9 and the putative metabolite ketone 10. These entities have been compared in the KKA(y) mouse model of human type-II diabetes to pioglitazone (2). Ketone 10 has proven to be the most potent of these thiazolidinediones in this in vivo assay. When 6-10 were compared in vitro in the 3T3-L1 cell line to 2, for their ability to augment insulin-stimulated lipogenesis, 10 was again the most potent compound with 6, 7, and 9 roughly equivalent to 2. These data suggest that metabolites 6, 7, and 9 are likely to contribute to the pharmacological activity of pioglitazone (2), as had been previously reported for ciglitazone (1).

Studies on antidiabetic agents. XII. Synthesis and activity of the metabolites of (±)-5-[p-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl]-2,4- thiazolidinedione (pioglitazone)

The metabolites of (±)-5-[p-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl]-2,4- thiazolidinedione (1, pioglitazone), which is a representative insulin- sensitizing agent, were synthesized to confirm their structures and for studies of their pharmacological properti

Hydroboration. 75. Directive Effects in the Hydroboration of Vinyl and Propenyl Heterocycles with Representative Hydroborating Agents

The hydroboration of representative heterocyclic compounds bearing a vinyl or propenyl substituent with borane-methyl sulfide (BMS), 9-borabicyclononane (9-BBN), dicyclohexylborane (Chx2BH), and disiamylborane (Sia2BH) was investigated systematically to establish directive effects in the hydroboration.The directive effects observed for 2-vinylfuran and 2-vinylthiophene are similar to those realized in styrene.The hydroboration of vinylpyridine required an excess of borane hydroborating agent.Alternatively, the nitrogen atom could be protected by complexing with boron trifluoride.When the vinyl group is ortho or para to the pyridine nitrogen, α-organoboranes are the major products in the hydroboration.However, when the vinyl group is meta to the pyridine nitrogen, β-organoboranes are formed predominantly.Hydroboration of the vinyl-pyridine-BF3 complexes results in an increase in the formation of α-organoboranes, as compared to β.The distribution of boron in the hydroboration of 2-propenyl heterocyclic compounds compared to that of trans-1-propenylbenzene showed that the effect of the heterocycle is pronounced in directing the boron atom strongly to the α-carbon atom.