13362-26-0

Basic information

• Product Name: Ethyl 2-aminopyridine-3-carboxylate
• Synonyms: Ethyl 2-aMinonicotinic acid;Ethyl 2-amino-3-pyridinecarboxylate;ethyl 2-aMinopyridin-3-carboxylate;RARECHEM AL BI 1234;AKOS 90517;2-AMINO-NICOTINIC ACID ETHYL ESTER;ETHYL 2-AMINONICOTINATE;BUTTPARK 23\07-65
• CAS NO: 13362-26-0
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• Product Categories: pharmacetical;API intermediates;Pyridine;Amines;Heterocycles
• Mol File: 13362-26-0.mol

Chemical Properties

• Melting Point: 96-98°C
• Boiling Point: 133°C/12mmHg(lit.)
• Flash Point: 115.126 °C
• Appearance: /Solid
• Density: 1.193 g/cm³
• Vapor Pressure: 0.008mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol
• PKA: 4.84±0.36(Predicted)
• CAS DataBase Reference: Ethyl 2-aminopyridine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-aminopyridine-3-carboxylate(13362-26-0)
• EPA Substance Registry System: Ethyl 2-aminopyridine-3-carboxylate(13362-26-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 13362-26-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 2-aminopyridine-3-carboxylate is used as a diuretic agent for its ability to increase urine output and help regulate the body's fluid balance. This application is particularly useful in treating conditions such as high blood pressure, heart failure, and kidney disorders.
Used in Research and Development:
As a pyrimidine derivative, Ethyl 2-aminopyridine-3-carboxylate is also utilized in research and development for the synthesis of various pharmaceutical compounds and the study of their potential therapeutic effects.
Used in Drug Delivery Systems:
Ethyl 2-aminopyridine-3-carboxylate can be employed in the development of drug delivery systems, where its chemical properties may contribute to the design of novel formulations that enhance the bioavailability and efficacy of other therapeutic agents.

InChI:InChI=1/C8H10N2O2/c1-2-12-8(11)6-4-3-5-10-7(6)9/h3-5H,2H2,1H3,(H2,9,10)

Upstream product

• 5345-47-1 2-aminopyridin-3-carboxylic acid 
• 64-17-5 ethanol 
• 5444-80-4 1,3,3-triethoxypropene 
• 27317-59-5 Ethyl 3-ethoxy-3-iminopropionate 
• 69142-53-6 2-[1-(3-Ethoxycarbonyl-pyridin-2-ylamino)-meth-(E)-ylidene]-succinic acid diethyl ester 
• 497-19-8 sodium carbonate 
• 75-03-6 ethyl iodide 
• 1452-94-4 ethyl 2-chloronicotinate 
• 199734-00-4 C₂₆H₂₃N₂O₂P 
• 105-56-6 ethyl 2-cyanoacetate 
• 289-96-3 1,2,3-triazine 

Downstream Products

• 109644-88-4 2-[(N-acetyl-sulfanilyl)-amino]-nicotinic acid ethyl ester 
• 5327-31-1 2-aminonicotinic acid hydrazide 
• 153687-09-3 4-hydroxy-3-(o-methoxyphenyl)-1,8-naphthyridin-2(1H)-one 
• 57073-56-0 2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-9-carboxylic acid 
• 138768-75-9 ethyl 2-[(4-methyl-phenylsulfonyl)amino]pyridine-3-carboxylate 
• 870997-87-8 2-amino-N-methyl-nicotinamide 
• 13438-65-8 2-aminopyridine-3-carboxamide 
• 158020-74-7 imidazo[1,2-a]pyridine-8-carboxylic acid ethyl ester 
• 181123-24-0 ethyl 2-amido-(N-[3-phenoxy]phenylacetyl)nicotinate 
• 372951-31-0 ethyl 2-amido-(N-phenylacetyl)nicotinate 
• 169495-51-6 ethyl 2-amino-5-chloronicotinate 
• 23612-57-9 (2-amino-3-pyridinyl)methanol 
• 652976-27-7 5-hydroxy-8-oxo-8,9-dihydro-7H-pyrido[2,3-b]azepine-6-carboxylic acid ethyl ester 
• 652976-28-8 6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepine-5,8-dione 

Relevant articles and documents

Fused Pyridine Derivatives from the Wittig Reaction of some Fluorinated Amides

Compound 2 reacted with phosphorane 3 (R = Et) giving the quinoline derivative 5 whereas thiophenes 7 and 9 gave enamines 8 and 10 respectively with the appropriate phosphorane 3 (R = Me or Et).Pyridine derivative 11 yielded only ethyl 2-aminonicotinate with phosphorane 3 (R = Et).Compounds 8 and 10 gave the fused pyridine derivatives 14 and 15 respectively.

9- and 11-substituted 4-azapaullones are potent and selective inhibitors of African trypanosoma

Trypanosomes from the "brucei" complex are pathogenic parasites endemic in sub-Saharan Africa and causative agents of severe diseases in humans and livestock. In order to identify new antitrypanosomal chemotypes against African trypanosomes, 4-azapaullone

SYNTHESIS, X-RAY STRUCTURE ANALYSIS, AND VIBRATIONAL SPECTRAL STUDIES OF 1-(3-((6-BROMOPYRIDO[2,3-d]PYRIMIDIN-4-YL) OXY)PHENYL)-3-CYCLOPENTYLUREA

Abstract: A new pyrido[2,3-d]pyrimidine derivative 1-(3-((6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy)phenyl)-3-cyclopentylurea is designed and synthesized. The final structure is characterized by 1H, 13C, and 2D NMR, MS, FTIR. In addition, the crystal structure of the title compound is determined by X-ray diffraction. With the 6-311G(2d,p) basis set, the molecule is further explored using density functional theory (DFT) by the B3LYP method. The final results show that the DFT optimized structure of the title molecule is consistent with the crystal structure determined by X-ray diffraction. The Hirshfeld surface analysis and the 2D fingerprint plot are given to support the quantitative analysis of intermolecular interactions and contacts generated by supramolecular accumulation in crystals. The interactions of the title molecule are analyzed by the natural bond orbital analysis. Finally, the molecular electrostatic potential and frontier molecular orbitals are further investigated using DFT. [Figure not available: see fulltext.]

Synthesis, crystal structure, and DFT study of a new pyrido[2,3-d]pyrimidine compound 1-(4-((6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy) phenyl)-3-(2,4-difluorophenyl)urea

In this study, 1-(4-((6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy)phenyl)-3- (2,4-difluorophenyl) urea was synthesized. The structure of the compound was determined by mass spectrometry and 1H NMR, 13C NMR and FT-IR spectroscopy. The solid-state structure of the title compound was determined using single-crystal X-ray diffraction and the optimized molecular structure was determined using density functional theory calculations. The conformation of the most stable isomer that was calculated at room temperature was consistent with the conformation derived from X-ray diffraction. Hirshfeld surface analysis and 2D fingerprints were used to quantitatively analyze the intermolecular interactions and contacts in the crystal structure.

Access to pyridines via cascade nucleophilic addition reaction of 1,2,3-triazines with activated ketones or acetonitriles

We studied the cascade nucleophilic addition reactions of 1,2,3-triazines with activated acetonitriles or ketones, which were used to construct highly substituted pyridines that are not easily accessed by conventional methods. The strategy addressed some structural diversity issues currently facing medicinal chemistry, and the resulting pyridines could be used as convenient precursors for the synthesis of related pharmaceuticals. In particular, our method was applied to the syntheses of the marketed drug etoricoxib and several biologically important molecules in a few steps.

Pyrido[2,3-d]pyrimidine compound as well as preparation method and application thereof

The present invention discloses a pyrido[2,3-d]pyrimidine compound represented by a general formula I or a pharmaceutically acceptable salt thereof. The general formula I is shown as the specification, wherein R1 is selected from one of an alkylamine group of C1-C6, an alicyclic amine group of C1-C6, a heterocyclic amine group of C1-C6, and an aromatic amine group of C6-C8, and X represents a hydrogen atom or a halogen atom. According to the invention, in-vitro cell activity tests prove that the compound provided by the invention has antitumor activity and can be used for preparing medicines for treating and/or preventing various cancers caused by BRaf kinase mutation, such as melanoma, thyroid cancer, breast cancer, liver cancer, kidney cancer, colorectal cancer, pancreatic cancer, ovarian cancer, etc.

Synthesis and antitumor activity of novel pyridino[2,3-d]pyrimidine urea derivatives

A series of novel N-(3-((6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy)phenyl)pyrrolidine-1-carboxamide and 1-(3-((6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy)phenyl)-3-propylurea derivatives were synthesized. Their antitumor activities against human breast carcinoma cells (MCF-7) and human colon cancer cells (HCT-116) in vitro were evaluated, using sorafenib as a positive control drug. Anticancer bioassays indicated that several compounds exhibited appreciable anticancer activity against MCF-7 and HCT-116 cells. Particularly, compounds 9g and 8b demonstrated the most significant inhibitory effect against HCT-116 and MCF-7 cells, with inhibition ratios of 25.56% and 26.46%, respectively. Additionally, the synthesized pyridine[2,3-d]pyrimidine derivatives containing a urea group moieties exhibited antitumor activities against MCF-7 and HCT-116 cells in vitro.

Synthesis, Crystal Structure, and DFT Study of a New Derivative of Pyrido[2,3-d]pyrimidine

Abstract: N-{4-[(6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy]phenyl}morpholine-4-carboxamide has been synthesized as a derivative of pyrido[2,3-d]pyrimidine that demonstrates antitumor, antibacterial, anti-inflammatory, and antimicrobial activities. Synthesis of the target compound based on 2-aminonicotinic acid as the starting material has included its esterification, bromination, cyclization, and substitution reactions. Structure of the product is confirmed by 1H and 13C NMR, FT-IR, and single-crystal X-ray diffraction (XRD). The optimized structure, electrostatic potential and frontier molecular orbitals (FMO) of the compound have been approached by DFT calculations. The compound demonstrates antiproliferative activity on A375 cells.

Synthesis method and applications of polysubstituted 2-aminopyridine derivative

The invention belongs to the field of organic synthetic chemistry, and relates to a synthetic method and applications of a polysubstituted 2-aminopyridine derivative. According to the method, a 1,2,3-triazine compound and a cyanomethyl compound are used as substrates and are subjected to a one-step cycloaddition reaction under an alkaline condition to obtain a polysubstituted 2-aminopyridine derivative, wherein the reaction does not involve in danger and control reagents and medicines, and a simple, safe, efficient and environment-friendly strategy is provided for synthesizing the polysubstituted 2-aminopyridine derivative. According to the present invention, the obtained product is subjected to further derivatization, such that the active molecule or the drug molecule containing the 2-aminopyridine structure can be synthesized, such as active molecule SC-53606, drug molecule apatinib and nevirapine.

PROCESS FOR THE CATALYTIC DIRECTED CLEAVAGE OF AMIDE-CONTAINING COMPOUNDS

The present invention relates to a catalytic method for the conversion of amide-containing compouds by means of a build-in directing group and upon the action of a heteronucleophilic compound (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or a thiol (RSH)) in the presence of a metal catalyst to respectively esters, thioesters, carbonates, thiocarbonates and to what is defined as amide-containing compounds (such as carboxamides, urea, carbamates, thiocarbamates). The present invention also relates to these amide-containing compounds having a build-in directing group (DG), as well as the use of such directing groups in the catalytic directed cleavage of N-DG amides with the use of heteronucleophiles (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or thiol (RSH)).