122321-04-4

Basic information

• Product Name: 2-N-Methyl-2-pyridylaminoethanol
• Synonyms: N-METHYL-N-(2-PYRIDYL)ETHANOLAMINE;2-[N-(2-HYDROXYETHYL)-N-METHYLAMINO]PYRIDINE;2-[(N-METHYL-N-2-PYRIDINYL) AMINO]ETHANOL;2-(N-METHYL-2-PYRIDYLAMINO)ETHANOL;2-[METHYL(2-PYRIDINYL)AMINO]-1-ETHANOL;2-(METHYL-2-PYRIDINYLAMINO)-ETHANOL;2-(METHYL-2-PYRIDYLAMINO)ETHANOL;IFLAB-BB F2108-0001
• CAS NO: 122321-04-4
• Molecular Formula: C₈H₁₂N₂O
• Molecular Weight: 152.19
• EINECS: 1312995-182-4
• Mol File: 122321-04-4.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 98-100°C 0,1mm
• Flash Point: 123.9 °C
• Appearance: clear light yellow to light brown viscous liquid
• Density: 1.13 g/cm³
• Vapor Pressure: 0.00172mmHg at 25°C
• Refractive Index: 1.5705-1.5735
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.59±0.10(Predicted)
• Water Solubility: Soluble in water.
• CAS DataBase Reference: 2-N-Methyl-2-pyridylaminoethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-Methyl-2-pyridylaminoethanol(122321-04-4)
• EPA Substance Registry System: 2-N-Methyl-2-pyridylaminoethanol(122321-04-4)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• HazardClass: IRRITANT
• Hazardous Substances Data: 122321-04-4(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow to light brown viscous liquid

Uses

2-Methyl-2-pyridylaminoethanol is used as a reagent to synthesize Rosiglitazone (Maleate: R693500), a thiazolinedione drug used to reduce insulin resistance in patients with Type 2 diabetes.

InChI:InChI=1/C8H12N2O/c1-10(6-7-11)8-4-2-3-5-9-8/h2-5,11H,6-7H2,1H3

Upstream product

• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 372-48-5 2-fluoropyridine 
• 109-09-1 2-chloropyridine 
• 109-04-6 2-bromo-pyridine 

Downstream Products

• 122320-74-5 5-{4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzylidene}thiazolin-2,4-dione 
• 219764-83-7 2-chloro-4-((2-(N-methyl-N-(2-pyridinyl)amino)ethyl)oxy)benzyl alcohol 
• 219764-84-8 2-chloro-4-((2-(N-methyl-N-(2-pyridinyl)amino)ethyl)oxy)benzyl chloride 
• 122321-03-3 4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde 

Relevant articles and documents

Preparation method of rosiglitazone

The invention provides a preparation method of rosiglitazone. The preparation method is characterized by comprising the following steps: reacting 2-chloropyridine with 2-methylaminoethanol under the catalysis of sodium triphenylmethyl to generate 2-[N-methyl-N-(2-pyridine) amino] ethanol; then carrying out Williamson synthesis reaction on the 2-[N-methyl-N-(2-pyridine) amino] ethanol and 4-fluorobenzaldehyde under the catalysis of bis (trimethylsilyl) amino potassium to obtain 4-[2-[N-methyl-N-(2-pyridine) amino] ethoxy] benzaldehyde; then carrying out condensation reaction with thiazoline-2,4-diketone to obtain 5-{4-[2-[N-methyl-N-(2-pyridine) amino] ethoxy] benzylidene} thiazoline-2, 4-diketone; and carrying out reduction reaction under the catalysis of an organic manganese reagent to obtain the rosiglitazone. The preparation method is simple, mild in condition, high in reaction yield and suitable for industrial production.

Synthetic optimization of rosiglitazone and related intermediates for industrial purposes

As an important newly Food and Drug Administration (FDA)-approved drug for treating diabetes, rosiglitazone (1) has received much attention from researchers in many areas. To search for an economical and convenient synthesis method for 1, we explored the reaction conditions and workup of a scalable five-step synthetic route by an orthogonal method to determine the best condition for each reaction step. The starting materials are commercially available, including 2-chloropyridine (2), N-methylethanolamine (3), 4-fluorobenzaldehyde (4a) or 4-hydroxybenzaldehyde (4b), and 1,3-thiazolidine-2,4-dione (5). The five sequential reaction steps are cyclization, alkylation, etherification, condensation, and reduction, having optimal yield of 90, 99, 59, 75, and 91 %, respectively. The best overall yield to synthesize rosiglitazone based on compound 2 was 40 %, being suitable for industrial purposes, using water as a green solvent and avoiding column chromatography during the last three reaction steps.

Design and synthesis of new potent PTP1B inhibitors with the skeleton of 2-substituted imino-3-substituted-5-heteroarylidene-1,3-thiazolidine-4-one: Part I

A new series of 2-substituted imino-3-substituted-5- heteroarylidene-1,3-thiazolidine-4-ones as the potent bidentate PTP1B inhibitors were designed and synthesized in this paper. All of the new compounds were characterized and identified by spectra analysis. The biological screening test against PTP1B showed that some of these compounds have the positive inhibitory activity against PTP1B. The activity of the compounds with 5-substituted pyrrole on 5-postion of 1,3-thiazolidine-4-one are more potent than that of those compounds with 5-substituted pyridine group. Compound 14b, 14h and 14i showed IC50values of 8.66?μM, 6.83?μM and 6.09?μM against PTP1B, respectively. Docking analysis of these active compounds with PTP1B showed the possible interaction modes of these biheterocyclic compounds with the active sites of PTP1B. The inhibition tests against oncogenetic CDC25B were also conducted on this set of compounds to evaluate the selectivity and possible anti-neoplastic activity. Compound 14b also showed the lowest IC50of 1.66?μM against CDC25B among all the possible inhibitors, including 14g, 14h, 14i and 15c. Some pharmacological parameters including VolSurf, steric and electric descriptors of all the compounds were calculated to give some hints about the relative relationship with the biological activity. The result of this study might give some light on designing the possible anti-cancer drugs targeting at phosphatases. The most active compound 14i might be used as the lead compound for further structure modification of the new low molecular weight PTP1B inhibitors with the N-containing heterocyclic skeleton.