2,5-Dioxopyrrolidin-1-YL 2-cyanoacetate

Base Information

• Chemical Name: 2,5-Dioxopyrrolidin-1-YL 2-cyanoacetate
• CAS No.: 56657-76-2
• Molecular Formula: C7H6N2O4
• Molecular Weight: 182.136
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID70697082
• Wikidata: Q82626904
• Mol file: 56657-76-2.mol

Synonyms:56657-76-2;2,5-DIOXOPYRROLIDIN-1-YL 2-CYANOACETATE;CYANOACETIC ACID-OSU;(2,5-dioxopyrrolidin-1-yl) 2-cyanoacetate;2,5-Pyrrolidinedione, 1-[(cyanoacetyl)oxy]-;Succinimidyl Cyanoacetate;2,5-Dioxopyrrolidin-1-yl cyanoacetate;3-[(2,5-dioxopyrrolidin-1-yl)oxy]-3-oxopropanenitrile;3-[(2,5-dioxopyrrolidin-1-yl)oxy]-3-oxopropane nitrile;SCHEMBL213096;DTXSID70697082;OZLIBRFWDOSHRS-UHFFFAOYSA-N;CS-M3397;MFCD00798802;AKOS006271994;AC-7193;AM85823;AS-18014;2,5-DIOXOPYRROLIDIN-1-YL2-CYANOACETATE;EN300-7374615;A869878;cyano-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester;ACETIC ACID, 2-CYANO-, 2,5-DIOXO-1-PYRROLIDINYL ESTER

Chemical Property of 2,5-Dioxopyrrolidin-1-YL 2-cyanoacetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.53
• Boiling Point: 336.064°C at 760 mmHg
• PKA: 0.74±0.10(Predicted)
• Flash Point: 157.046°C
• PSA: 87.47000
• Density: 1.468g/cm³
• LogP: -0.55482
• Storage Temp.: 2-8°C
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 182.03275668
• Heavy Atom Count: 13
• Complexity: 298

Purity/Quality:

99% ^*data from raw suppliers

CyanoaceticAcidN-HydroxysuccinimideEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)CC#N
• Uses: Cyanoacetic Acid N-Hydroxysuccinimide Ester is used as a pharmaceutical intermediate. It is used in the preparation of substituted pyrrolopyrimidinamines as selective Janus kinase inhibitors for the treatment of autoimmune diseases and organ transplant rejection.

Technology Process of 2,5-Dioxopyrrolidin-1-YL 2-cyanoacetate

There total 2 articles about 2,5-Dioxopyrrolidin-1-YL 2-cyanoacetate 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: 25.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + cyanoacetic acid (372-09-8) → succinimidyl cyanoacetate (56657-76-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran;

Reference yield:

→ succinimidyl cyanoacetate (56657-76-2)

Guidance literature:

Reference yield: 97.0%

(R)-6-(4-(benzyloxy)phenyl)-5-fluoro-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)-N-(piperidin-3-yl)pyrimidin-4-amine + succinimidyl cyanoacetate (56657-76-2) → (R)-3-(3-((6-(4-(benzyloxy)phenyl)-5-fluoro-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

cyanoacetic acid

Downstream raw materials:

N-[2-benzyloxy-3-(2-cyanoacetylamino)propyl]-2-cyanoacetamide

N-{2-(2-cyanoacetylamino)-1-[1-(2-cyanoacetylamino)methyl]ethyl}benzamide

tasocitinib

Tofacitinib citrate

Refernces

• 1、 -. "THERAPEUTIC AGENTS". Page/Page column 29-30. . Retrieved 2010/04/03.
• 2、 Stefanowicz, P.,Siemion, I. Z.. "REACTIVITY OF N-HYDROXYSUCCINIMIDE ESTERS". . p. 111 - 118. Retrieved 2007/10/02.