ethyl 3-pyridin-4-yl-1,2,4-oxadiazole-5-carboxylate

Base Information

• Chemical Name: ethyl 3-pyridin-4-yl-1,2,4-oxadiazole-5-carboxylate
• CAS No.: 163719-72-0
• Molecular Formula: C₁₀H₉N₃O₃
• Molecular Weight: 219.2
• Hs Code.: 2933399990
• Mol file: 163719-72-0.mol

Synonyms:ethyl 3-pyridin-4-yl-1,2,4-oxadiazole-5-carboxylate;Ethyl 3-pyridin-3-yl-[1,2,4]oxadiazole-5-carboxylate;3-(Pyridin-3-yl)-1,2,4-oxadiazole-5-carboxylic acid ethyl ester

Chemical Property of ethyl 3-pyridin-4-yl-1,2,4-oxadiazole-5-carboxylate

Chemical Property:

• Vapor Pressure: 1.05E-05mmHg at 25°C
• Boiling Point: 371.2°C at 760 mmHg
• PKA: 1.23±0.12(Predicted)
• Flash Point: 178.3°C
• PSA: 78.11000
• Density: 1.277g/cm³
• LogP: 1.30830
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl3-pyridin-3-yl-[1,2,4]oxadiazole-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 3-pyridin-4-yl-1,2,4-oxadiazole-5-carboxylate

There total 2 articles about ethyl 3-pyridin-4-yl-1,2,4-oxadiazole-5-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 54.0%

nicotinamide oxime (1594-58-7) + Ethyl oxalyl chloride (4755-77-5) → ethyl [3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl]carboxylate (163719-72-0)

Guidance literature:

With pyridine; In chloroform; at 20 ℃; for 5.5h; Reflux;

DOI:10.1016/j.bmcl.2007.11.121

Reference yield:

pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) → ethyl [3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl]carboxylate (163719-72-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydroxylamine hydrochloride; potassium carbonate / ethanol / 16 h / Heating

2.1: 4A molecular sieves; NaH / tetrahydrofuran / 0.1 h

2.2: 28 percent / tetrahydrofuran / 1 h / Heating

With 4 A molecular sieve; hydroxylamine hydrochloride; sodium hydride; potassium carbonate; In tetrahydrofuran; ethanol;

DOI:10.1021/jm0407613

Reference yield:

C14H23N3 + ethyl [3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl]carboxylate (163719-72-0) → C22H26N6O2

Guidance literature:

In ethanol; for 8h; Reflux;

DOI:10.1016/j.bmcl.2007.11.121

upstream raw materials:

nicotinamide oxime

Ethyl oxalyl chloride

pyridine-3-carbonitrile

Downstream raw materials:

Z₀₆₆-0014

Z₀₆₆-0150

Z₀₆₆-0034

E₂₁₃-2157

Refernces

• 1、 Huhtiniemi, Tero,Suuronen, Tiina,Rinne, Valtteri M.,Wittekindt, Carsten,Lahtela-Kakkonen, Maija,Jarho, Elina,Wallén, Erik A. A.,Salminen, Antero,Poso, Antti,Lepp?nen, Jukka. "Oxadiazole-carbonylaminothioureas as SIRT1 and SIRT2 inhibitors". supporting information; experimental part. p. 4377 - 4380. Retrieved 2009/06/17.