41051-03-0

Basic information

• Product Name: ethyl 5-cyano-2-pyridinecarboxylate
• Synonyms: ethyl 5-cyano-2-pyridinecarboxylate;ethyl 5-cyanopicolinate;5-Cyano-pyridine-2-carboxylic acid ethyl ester
• CAS NO: 41051-03-0
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.18
• Mol File: 41051-03-0.mol

Chemical Properties

• Melting Point: 74-76°
• Boiling Point: 333°Cat760mmHg
• Flash Point: 155.2°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 0.000141mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: ethyl 5-cyano-2-pyridinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5-cyano-2-pyridinecarboxylate(41051-03-0)
• EPA Substance Registry System: ethyl 5-cyano-2-pyridinecarboxylate(41051-03-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 41051-03-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 5-cyano-2-pyridinecarboxylate is used as a synthetic intermediate for the preparation of substituted pyrrolidine-2-carboxamides. These compounds act as antagonists of the interaction between the p53 and MDM2 proteins, which play a crucial role in regulating the cell cycle and apoptosis. By disrupting this interaction, these antagonists can potentially serve as anticancer agents, offering a new avenue for cancer treatment and therapy.

InChI:InChI=1/C9H8N2O2/c1-2-13-9(12)8-4-3-7(5-10)6-11-8/h3-4,6H,2H2,1H3

Upstream product

• 617-35-6 2-oxo-propionic acid ethyl ester 
• 100-54-9 pyridine-3-carbonitrile 
• 17874-78-1 6-ethoxycarbonylpyridine-3-carboxylic acid 
• 100-26-5 Pyridine-2,5-dicarboxylic acid 
• 67515-95-1 5-chlorocarbonyl-pyridine-2-carboxylic acid ethyl ester 

Downstream Products

• 788801-45-6 [tert-butoxycarbonyl-(1-cyclohexylmethyl-2-{2-[(6-methylsulfanylcarbonimidoyl-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-2-oxo-ethyl)-amino]-acetic acid tert-butyl ester 
• 182291-44-7 [tert-butoxycarbonyl-(1-cyclohexylmethyl-2-oxo-2-{2-[(6-thiocarbamoyl-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-ethyl)-amino]-acetic acid tert-butyl ester 
• 182291-43-6 tert-butyl {(tert-butoxycarbonyl)[(1R)-2-[(2S)-2-({[(6-cyano-3-pyridinyl)methyl]amino}carbonyl)-2,5-dihydro-1H-pyrrol-1-yl]-1-(cyclohexylmethyl)-2-oxoethyl]amino}acetate 
• 182159-74-6 ((R)-2-{(S)-2-[(6-Carbamoyl-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester 
• 182291-42-5 ((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic acid tert-butyl ester 
• 182159-75-7 ((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester 
• 302341-61-3 tert-bulyl N-[(6-cyanopyridin-3-yl)methyl]carbamate 
• 65346-04-5 5-cyano-2-pyridinecarboxamide 

Relevant articles and documents

Technical scale synthesis of a new and highly potent thrombin inhibitor

In this account, we describe the development of an efficient and convergent process for the peptidomimetic thrombin inhibitor 1 on production plant scale. Starting from nicotinonitrile (13), (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-2- pyrrolidinecarboxylic acid (5) and (2R)-2-amino-3-cyclohexylpropanoic acid (29) compound 1 was obtained in 16 chemical steps. New methods had been developed for the preparation of the key intermediate dehydroproline 22 and the transformation of nitriles into amidines. The thrombin inhibitor 1 was isolated by special techniques (nanofiltration and spray drying). Almost all salts of 1 are amorphous, however, a crystalline complex was obtained with 1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Saccharin).

HOMOLYTIC ALKOXYCARBONYLATION REACTIONS IN TWO-PHASE SYSTEMS 3. INTRODUCTION OF A SINGLE CARBOXYLIC ACID ESTER FUNCTION INTO CYANO- OR ALKOXYCARBONYL SUBSTITUTED N-HETEROAROMATICS

Homolytic alkoxycarbonylation reactions with cyanopyridines 1a, 2a, 3a, alkyl pyridinecarboxylates 1b, 2b, 3b, 3c and ethyl 4-pyridazinecarboxylate 4 in presence of dichloromethane were studied.It is demonstrated that under these conditions multiple substitution in general is suppressed markedly.Thus, this experimentally simple procedure represents an efficient and versatile method for single-step preparations of alkyl cyanopyridinecarboxylates 7a, 8a, 9a, 10a.Furthermore, it provides convenient access to so far not available mixed esters 5b, 7b, 8b, 10b, 13, derived from 2,3-pyridine-, 2,4-pyridine-, 3,4-pyridine and 4,5-pyridazinedicarboxylic acid.