4'-((2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile

Base Information

• Chemical Name: 4'-((2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile
• CAS No.: 138401-24-8
• Molecular Formula: C25H27N3O
• Molecular Weight: 385.509
• Hs Code.: 2933990090
• European Community (EC) Number: 423-500-4,604-075-6
• DSSTox Substance ID: DTXSID20431716
• Nikkaji Number: J570.366B
• Wikidata: Q72514465
• Pharos Ligand ID: ZP52K64JQPHJ
• ChEMBL ID: CHEMBL332051
• Mol file: 138401-24-8.mol

Synonyms:138401-24-8;4'-((2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile;4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]biphenyl-2-carbonitrile;[1,1'-Biphenyl]-2-carbonitrile, 4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-;2-Butyl-3-[[2'-cyano-[1,1'-biphenyl]-4-yl]methyl]-1,3-diazaspiro[4,4]non-1-en-4-one;CHEMBL332051;2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]phenyl]benzonitrile;4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-Biphenyl]-2-carbonitrile;4'-[(2-n-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile;EC 423-500-4;EC 604-075-6;4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl][1,1'-biphenyl]-2-carbonitrile;4'-[(2-BUTYL-4-OXO-1,3-DIAZASPIRO[4.4]NON-1-EN-3-YL)METHYL]-(1,1'-BIPHENYL)-2-CARBONITRILE;4'-[(2-N-BUTYL-4-OXO-1,3-DIAZASPIRO[4.4]NON-1-EN-3-YL)METHYL]-(1,1'-BIPHENYL)-2-CARBONITRILE;[1,1'-Biphenyl]-2-carbonitrile,4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl];4'-((2-butyl-4-oxo-1,3-diazaspiro(4.4)non-1-ene-3-yl)methyl)(1,1'-biphenyl)-2-carbonitrile;4'-((2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)biphenyl-2-carbonitrile;1,3-Diazaspiro[4.4]nonane, [1,1'-biphenyl]-2-carbonitrile deriv.;2-Butyl-3-[[2'-(cyano)biphenyl-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one;4'-((2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-ene-3-yl)methyl)(1,1'-biphenyl)-2-carbonitrile;4'-((2-n-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-(1,1'-biphenyl)-2-carbonitrile;4'-((2-n-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile;4'-[[2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl]methyl][1,1'-biphenyl]-2-carbonitrile;SCHEMBL1316335;DTXSID20431716;BCP13496;AC-125;BDBM50042242;MFCD06658242;AKOS015895294;AB25775;AM90288;2-[4-[(8-butyl-6-oxo-7,9-diazaspiro[4.4]non-8-en-7-yl)methyl]phenyl]benzonitrile;AC-20377;AS-13565;B4143;CS-0324405;FT-0601482;S11999;A807385;J-007132;2-(n-butyl)-3-[[2'-(cyano)biphenyl-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one;2-n-butyl-3-[(2'-cyanobiphenyl-4-yl)methyl]-1,3-diazaspiro-[4,4]-non-1-en-4-one;2-n-butyl-3-[[2'-cyanobiphenyl-4-yl]methyl]-1,3-diazaspiro-[4.4]non-1-en-4-one;4''-(2-butyl-4-oxo-1,3-diaza-spiro[4,4]-non-1-en-3-ylmethyl)-biphe-nyl-2-carbonitrile;4''-(2-Butyl-4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-ylmethyl)-biphenyl-2-carbonitrile;4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]nona-1-ene-3-yl)methyl]biphenyl-2-carbonitrile;2-[4-[(8-butyl-6-oxidanylidene-7,9-diazaspiro[4.4]non-8-en-7-yl)methyl]phenyl]benzenecarbonitrile;4'-[(2-butyl-4-oxo-1,3-diazaspiro[4,4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile;4'-[(2-n-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl](1,1'-biphenyl)-2-carbonitrile;4'-[[2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl]methy][1,1'-biphenyl]-2-carbonitrile;4'-[[2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3yl]methyl][1,1'-biphenyl]-2-carbonitrile

Chemical Property of 4'-((2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile

Chemical Property:

• Appearance/Colour: White or off-white crystalline powder
• Vapor Pressure: 0Pa at 20℃
• Melting Point: 95-97°C
• Boiling Point: 576.5 °C at 760 mmHg
• PKA: 2.45±0.20(Predicted)
• Flash Point: 302.5 °C
• PSA: 56.46000
• Density: 1.151 g/cm³
• LogP: 4.84248
• Storage Temp.: Refrigerator
• Solubility.: soluble in Methanol
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 385.215412493
• Heavy Atom Count: 29
• Complexity: 661

Purity/Quality:

99% ^*data from raw suppliers

4''-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1''-Biphenyl]-2-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1=NC2(CCCC2)C(=O)N1CC3=CC=C(C=C3)C4=CC=CC=C4C#N
• Uses: 4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-(1,1'-biphenyl)-2-carbonitrile is a butyldiazaspirononenone derivative used in the preparation of acetylcholinesterase inhibitors. An impurity found in Irbesartan (I751000).

Technology Process of 4'-((2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile

There total 39 articles about 4'-((2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile 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: 90.0%

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) + 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride → 4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile (138401-24-8)

Guidance literature:

In N,N-dimethyl-formamide; for 0.0208333h; microwave irradiation;

DOI:10.1016/j.bmc.2007.07.014

Reference yield: 90.0%

N-pentanoylaminocyclopentane-1-carboxylic acid (15026-80-9) + [(2'-cyanobiphenyl-4-yl)methyl]amine (133690-92-3) → 4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile (138401-24-8)

Guidance literature:

N-pentanoylaminocyclopentane-1-carboxylic acid; [(2'-cyanobiphenyl-4-yl)methyl]amine; With methanesulfonic acid; In toluene; at 20 ℃; for 48h; Heating / reflux;

With sodium hydroxide; In water; toluene; for 0.5h; Product distribution / selectivity;

Reference yield: 90.0%

1-pentanoylamino-cyclopentanecarboxylic acid (2'-cyano-biphenyl-4-ylmethyl)-amide (141745-71-3) → 4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile (138401-24-8)

Guidance literature:

1-pentanoylamino-cyclopentanecarboxylic acid (2'-cyano-biphenyl-4-ylmethyl)-amide; With toluene-4-sulfonic acid; In toluene; for 18h; Reflux;

With sodium hydroxide; In water; toluene; pH=6.59; Product distribution / selectivity;

upstream raw materials:

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile

2-butyl-1,3-diaza-spiro[4.4]non-1-en-4one

copper(I) cyanide

2-Butyl-3-(2'-iodo-biphenyl-4-ylmethyl)-1,3-diaza-spiro[4.4]non-1-en-4-one

Downstream raw materials:

trityl irbesartan

irbesartan

2-n-butyl-4-spirocyclopentane-1-[((2'-tetrazol-5-yl)biphenyl-4-yl)methyl]-2-imidazolin-5-one hydrochloride

2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one

Refernces

• 1、 -. "One-pot method for preparing irbesartan". Paragraph 0026; 0029; 0032. . Retrieved 2018/12/13.
• 2、 Kumar, Manian Rajesh,Park, Kyungho,Lee, Sunwoo. "Synthesis of amido-N-imidazolium salts and their applications as ligands in suzuki-miyaura reactions: Coupling of hetero- aromatic halides and the synthesis of milrinone and irbesartan". experimental part. p. 3255 - 3266. Retrieved 2011/02/23.