Montelukast nitrile

Base Information

• Chemical Name: Montelukast nitrile
• CAS No.: 866923-62-8
• Molecular Formula: C35H35ClN2OS
• Molecular Weight: 567.195
• UNII: YS7B2ZWL9Z
• Metabolomics Workbench ID: 57143
• Wikidata: Q27121413
• Mol file: 866923-62-8.mol

Synonyms:montelukast nitrile;866923-62-8;Montelukast Cyclopropaneacetonitrile;MOK-1 nitrile;YS7B2ZWL9Z;Montelukast nitrile impurity;2-[1-[[(1R)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanylmethyl]cyclopropyl]acetonitrile;(R,E)-2-(1-((1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propylthio)methyl)cyclopropyl)acetonitrile;{1-[({(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl}sulfanyl)methyl]cyclopropyl}acetonitrile;2-(1-((1-(3-((E)-2-(7-Chloroquinolin-2-yl)ethenyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanylmethyl)cyclopropyl)acetonitrile;Cyclopropaneacetonitrile, 1-((((1R)-1-(3-((1E)-2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)-;UNII-YS7B2ZWL9Z;SCHEMBL1135035;SCHEMBL1135039;CHEBI:48970;LFNFSZSLPYLMBG-LDXVMNHOSA-N;Q27121413;1-[[[(1R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetonitrile

Chemical Property of Montelukast nitrile

Chemical Property:

• PSA: 82.21000
• LogP: 9.38698
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 566.2158626
• Heavy Atom Count: 40
• Complexity: 893

Purity/Quality:

>95% ^*data from raw suppliers

MontelukastCyclopropaneacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C1=CC=CC=C1CCC(C2=CC=CC(=C2)C=CC3=NC4=C(C=CC(=C4)Cl)C=C3)SCC5(CC5)CC#N)O
• Isomeric SMILES: CC(C)(C1=CC=CC=C1CC[C@H](C2=CC=CC(=C2)/C=C/C3=NC4=C(C=CC(=C4)Cl)C=C3)SCC5(CC5)CC#N)O
• Uses: Montelukast Cyclopropaneacetonitrile is an impurity in the synthesis of Montelukast (M568000), a selective leukotriene D4-receptor antagonist. Used as an antiasthmatic.

Technology Process of Montelukast nitrile

There total 14 articles about Montelukast nitrile 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: 98.9%

1-(mercaptomethyl)cyclopropane acetonitrile (866923-64-0) + 2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol (807638-71-7) → 2-(1-((((R)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)acetonitrile (866923-62-8)

Guidance literature:

With dmap; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 2.5h; Inert atmosphere;

Reference yield: 75.0%

(R,E)-((1-((1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)methyl methanesulfonate + sodium cyanide (143-33-9,25596-52-5) → 2-(1-((((R)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)acetonitrile (866923-62-8)

Guidance literature:

In N,N-dimethyl-formamide; at 60 ℃; for 18h;

Reference yield:

1-(mercaptomethyl)cyclopropane acetonitrile (866923-64-0) + (S)-benzenepropanol α-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methyl ethyl)-α-methane sulfonate (920739-17-9) → 2-(1-((((R)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)acetonitrile (866923-62-8)

Guidance literature:

1-(mercaptomethyl)cyclopropane acetonitrile; With n-butyllithium; In hexane; N,N-dimethyl-formamide; at -17 - -13 ℃; for 0.333333 - 0.5h;

(S)-benzenepropanol α-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methyl ethyl)-α-methane sulfonate; In hexane; N,N-dimethyl-formamide; at -17 - -13 ℃; for 1h;

upstream raw materials:

(1-[(1(R)-(3-((E)-2-(7-chloroquinolin-2-yl)ethenyl)phenyl)-3-(2-(1-(tetrahydropyran-2-yloxy)-1-methylethyl)phenyl)propyl)thiomethyl]cyclopropyl)acetonitrile

sodium cyanide

1-(mercaptomethyl)cyclopropane acetonitrile

(S)-benzenepropanol α-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methyl ethyl)-α-methane sulfonate

Downstream raw materials:

(R,E)-2-((1-((1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)acetamide

2-(2-((R)-3-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(((1-(hydroxymethyl)cyclopropyl)methyl)sulfanyl)propyl) phenyl)propan-2-ol

(S,E)-1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propan-1-ol

montelukast

Refernces

• 1、 Saravanan,Satyanarayana,Reddy, P. Pratap. "New and practical synthesis of montelukast sodium, an antiasthmatic drug". . p. 2050 - 2056. Retrieved 2013/06/27.
• 2、 -. "PROCESS". Page/Page column 28. . Retrieved 2008/06/13.