52505-56-3

Basic information

• Product Name: ETHYL 3-AMINO-4,6-DIMETHYLTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE
• Synonyms: AKOS USSH-4110705;AKOS BBS-00002565;AKOS 90099;ETHYL 3-AMINO-4,6-DIMETHYLTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE;BUTTPARK 59\40-63;3-Amino-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylic acid ethyl ester
• CAS NO: 52505-56-3
• Molecular Formula: C₁₂H₁₄N₂O₂S
• Molecular Weight: 250.32
• Mol File: 52505-56-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 404.1°Cat760mmHg
• Flash Point: 198.2°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 9.72E-07mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: ETHYL 3-AMINO-4,6-DIMETHYLTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-AMINO-4,6-DIMETHYLTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE(52505-56-3)
• EPA Substance Registry System: ETHYL 3-AMINO-4,6-DIMETHYLTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE(52505-56-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 52505-56-3(Hazardous Substances Data)

Usage

Description

ETHYL 3-AMINO-4,6-DIMETHYLTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE is an organic compound that serves as a crucial intermediate in the synthesis of various dyes. It is characterized by its unique molecular structure, which includes a thieno[2,3-b]pyridine core with an ethyl carboxylate group and an amino substituent. ETHYL 3-AMINO-4,6-DIMETHYLTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE is known for its potential applications in the textile industry, particularly in the development of dyes for polyamide and polyester fibers.

Uses

Used in Textile Industry:
ETHYL 3-AMINO-4,6-DIMETHYLTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE is used as an intermediate in the synthesis of dyes for [application reason] the production of vibrant and long-lasting colors in polyamide and polyester fibers. Its role in the dye manufacturing process is essential, as it contributes to the development of dyes with improved properties, such as enhanced colorfastness and reduced environmental impact.
As an intermediate in the preparation of 2-[[4-(Arylazo)-3,5-disubstituted-pyrazol-1-yl]carbonyl]thieno[2,3-b]pyridine dyes, ETHYL 3-AMINO-4,6-DIMETHYLTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE plays a significant role in the textile industry. These dyes are specifically designed for use with polyamide and polyester fibers, which are widely used in the production of various types of fabrics, clothing, and other textile products. The dyes derived from this intermediate are known for their ability to produce vibrant and long-lasting colors, making them highly desirable in the textile market.

InChI:InChI=1/C12H14N2O2S/c1-4-16-12(15)10-9(13)8-6(2)5-7(3)14-11(8)17-10/h5H,4,13H2,1-3H3

Upstream product

• 14237-71-9 2-chloro-4,6-dimethylnicotinonitrile 
• 623-51-8 ethyl 2-sulfanylacetate 
• 54585-47-6 3-cyano-4,6-dimethyl-2-mercaptopyridine 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-53-3 diethyl malonate 
• 61889-26-7 3-bromo-4,6-dimethyl-isothiazolo[5,4-b]pyridine 
• 128257-06-7 2-(3-Cyano-4,6-dimethyl)pyridyl (ethoxycarbonyl)methyl sulfide 
• 54585-47-6 4,6-Dimethyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile 
• 105-36-2 ethyl bromoacetate 
• 105855-62-7 3-Cyano-4,6-dimethyl-2-thiono-pyridine 

Downstream Products

• 58327-76-7 3-amino-2-carboxylic acid-4,6-dimethylthieno[2,3-b]pyridine 
• 128918-28-5 3-Amino-4,6-dimethylthieno<2,3-b>pyridine-2-carbohydrazide 
• 144254-93-3 Sodium; 3-amino-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylate 
• 132602-58-5 7,9-Dimethyl-4-oxo-2-phenyl-4H-pyrido<3',2':4,5>thieno<3,2-d>(1,3)oxazine 
• 145916-76-3 7,9-Dimethyl-2-phenyl-3H-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4-one 
• 128991-43-5 7,9-Dimethyl-3-phenyl-2-thiopyrido<3',2':4,5>thieno<3,2-d>pyrimidine-2,4(1H,3H)-dione 
• 55023-35-3 7,9-dimethylpyrido[3',2':4,5]thieno[3,2-d]pyrimidine-4(1H)-one 
• 960059-50-1 3-amino-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylic acid 2-oxo-2-phenyl-ethyl ester 
• 911832-80-9 9,11-dimethyl-3-phenyl-pyrido[3'',2'':4',5']thieno[3',2':4,5]pyrimido[2,1-b][1,3,4]thiadiazin-6-one 
• 911832-74-1 1-[3-amino-7,9-dimethyl-4-oxo-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-2-yl]thio-1-(N-phenylhydrazono)-2-oxo-propane 
• 911832-75-2 ethyl 2-[3-amino-7,9-dimethyl-4-oxo-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-2-yl]thio-2-[N-(4-methylphenyl)hydrazono]-ethanoate 
• 911832-76-3 2-[3-amino-7,9-dimethyl-4-oxo-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-2-yl]thio-2-[N-(4-methylphenyl)hydrazono]-1-phenylethanone 
• 99504-81-1 3-(p-nitrobenzylideneamino)-2,7,9-trimethyl pyrido<3',2':4,5>thieno-<3,2-d>pyrimidin-4(3H)one 

Relevant articles and documents

Novel M4 positive allosteric modulators derived from questioning the role and impact of a presumed intramolecular hydrogen-bonding motif in β-amino carboxamide-harboring ligands

This letter describes a focused exercise to explore the role of the β-amino carboxamide moiety found in all of the first generation M4 PAMs and question if the NH2 group served solely to stabilize an intramolecular hydrogen bond (IMHB) and enforce planarity. To address this issue (and to potentially find a substitute for the β-amino carboxamide that engendered P-gp and contributed to solubility liabilities), we removed the NH2, generating des-amino congeners and surveyed other functional groups in the β-position. These modifications led to weak M4 PAMs with poor DMPK properties. Cyclization of the β-amino carboxamide moiety by virtue of a pyrazole ring re-enforced the IMHB, led to potent (and patented) M4 PAMs, many as potent as the classical bicyclic β-amino carboxamide analogs, but with significant CYP1A2 inhibition. Overall, this exercise indicated that the β-amino carboxamide moiety most likely facilitates an IMHB, and is essential for M4 PAM activity within classical bicyclic M4 PAM scaffolds.

POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4

Disclosed herein are thieno[2,3-b:5,4-c']dipyridin-8-amine and pyrido[4',3':4,5]thieno[2,3-c]pyridazin-8-amine compounds, which may be useful as positive allosteric modulators of the muscarinic acetylcholine receptor M4 (mAChR M4). A

Synthesis, reactions and biological activity of 2-substituted 3-cyano-4,6-dimethylpyridine derivatives

The reaction of 2-chloro-4,6-dimethylpyridine-3-carbonitrile with hydrazine hydrate, hydroxylamine, and anthranilic acid afforded the corresponding pyrazolo, isoxazolo, and pyridoquinazoline derivatives. Alkylation of 2-mercapto-4,6-dimethylpyridine-3-carbonitrile with ethyl chloroacetate or phenacyl bromide followed by cyclization in NaOH gave thienopyridine derivatives. Diazotization of ethyl 3-amino-4,6-dimethylthieno[2,3-b]pyridine-2- carboxylate followed by the reaction with thiourea, guanidine carbonate, and hydroxylamine hydrochloride gave the corresponding thienopyridine derivatives. The biological activity of some new compounds has been discussed.