Setileuton

Base Information

• Chemical Name: Setileuton
• CAS No.: 910656-27-8
• Molecular Formula: C22H17F4N3O4
• Molecular Weight: 463.38200
• UNII: 0U2750935P
• ChEMBL ID: CHEMBL2105653
• NCI Thesaurus Code: C152347
• Wikidata: Q27237249
• Mol file: 910656-27-8.mol

Synonyms:4-(4-fluorophenyl)-7-(((5-(1-hydroxy-1-(trifluoromethyl)propyl)-1,3,4-oxadiazol-2-yl)amino)methyl)-2H-1-benzopyran-2-one;setileuton

Chemical Property of Setileuton

Chemical Property:

• PSA: 104.62000
• Density: 1.478
• LogP: 4.17600
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 6
• Exact Mass: 463.11551868
• Heavy Atom Count: 33
• Complexity: 744

Purity/Quality:

97% ^*data from raw suppliers

MK-0633 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1=NN=C(O1)NCC2=CC3=C(C=C2)C(=CC(=O)O3)C4=CC=C(C=C4)F)(C(F)(F)F)O
• Isomeric SMILES: CC[C@](C1=NN=C(O1)NCC2=CC3=C(C=C2)C(=CC(=O)O3)C4=CC=C(C=C4)F)(C(F)(F)F)O
• Recent ClinicalTrials: The Effect of MK 0633 in Patients With Atherosclerosis (0633-008)(COMPLETED)
• Recent EU Clinical Trials: A Double-Blind, Randomized, Placebo-Controlled, Multicenter, Parallel-Group, Dose-

Technology Process of Setileuton

There total 3 articles about Setileuton 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: 64.5%

4-(4-fluorophenyl)-2-oxo-2H-chromene-7-carboxaldehyde (910656-32-5) + (2S)-2-(5-amino-1,3,4-oxadiazol-2-yl)-1,1,1-trifluorobutan-2-ol (1222175-45-2) → Setileuton (910656-27-8)

Guidance literature:

4-(4-fluorophenyl)-2-oxo-2H-chromene-7-carboxaldehyde; (2S)-2-(5-amino-1,3,4-oxadiazol-2-yl)-1,1,1-trifluorobutan-2-ol; In toluene; Reflux;

With sodium tetrahydroborate; In methanol;

DOI:10.1021/jo100561u

Reference yield:

4-(4-fluorophenyl)-7-[({5-[(2S)-1,1,1-trifluoro-2-hydroxybutan-2-yl]-1,3,4-oxadiazol-2-yl}amino)methyl]-2H-chromen-2-one → (R)-4-(4-fluorophenyl)-7-[({5-[(2S)-1,1,1-trifluoro-2-hydroxybutan-2-yl]-1,3,4-oxadiazol-2-yl}amino)methyl]-2H-chromen-2-one + Setileuton (910656-27-8)

Guidance literature:

In ethanol; hexane; CHIRALPAK AD.(R). Resolution of racemate;

Reference yield:

C22H19F4N3O4S (1229617-81-5) → Setileuton (910656-27-8)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; at 67 ℃; for 18h; Inert atmosphere; Large scale reaction;

DOI:10.1021/jo100561u

upstream raw materials:

4-(4-fluorophenyl)-2-oxo-2H-chromene-7-carboxaldehyde

(2S)-2-(5-amino-1,3,4-oxadiazol-2-yl)-1,1,1-trifluorobutan-2-ol

C₂₂H₁₉F₄N₃O₄S

Downstream raw materials:

(1S)-N-([4-(4-fluorophenyl)-2-oxo-2H-chromen-7-yl]methyl)-5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3,4-oxadiazol-2-aminium4-methylbenzenesulfonate

(S)-4-(4-fluorophenyl)-7-[({5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3,4-oxadiazol-2-yl}amino)-methyl]-2H-chromen-2-one benzenesulfonate

Refernces

• 1、 Ducharme, Yves,Blouin, Marc,Brideau, Christine,Chateauneuf, Anne,Gareau, Yves,Grimm, Erich L.,Juteau, Helene,Laliberte, Sebastien,MacKay, Bruce,Masse, Frederic,Ouellet, Marc,Salem, Myriam,Styhler, Angela,Friesen, Richard W.. "The discovery of setileuton, a potent and selective 5-lipoxygenase inhibitor". scheme or table. p. 170 - 174. Retrieved 2010/10/21.