Semagacestat

Base Information

• Chemical Name: Semagacestat
• CAS No.: 425386-60-3
• Deprecated CAS: 866488-53-1,1644443-23-1
• Molecular Formula: C₁₉H₂₇N₃O₄
• Molecular Weight: 361.441
• Hs Code.: 29337900
• UNII: 3YN0602W4W
• DSSTox Substance ID: DTXSID10235740
• Nikkaji Number: J2.390.762C,J2.730.191F
• Wikipedia: Semagacestat
• Wikidata: Q426010
• NCI Thesaurus Code: C81115
• Pharos Ligand ID: TFZ8K89F5L52
• Metabolomics Workbench ID: 153448
• ChEMBL ID: CHEMBL520733
• Mol file: 425386-60-3.mol

Synonyms:LY 411,575;LY 411575;LY 450139;LY-411,575;LY-411575;LY411,575;LY411575;LY450139;N2-((2S)-2-(3,5-difluorophenyl)-2-hydroxyethanoyl)-N1-((7S)-5-methyl-6-oxo-6,7-dihydro-5H-dibenzo(b,d)azepin-7-yl)-L-alaninamide;N2-(2-(3,5-difluorophenyl)-2-hydroxyethanoyl)-N1-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo(b,d)azepin-7-yl)alaninamide;Semagacestat

Chemical Property of Semagacestat

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 208-212 °C
• Refractive Index: 1.576
• Boiling Point: 681.904 °C at 760 mmHg
• PKA: 12.97±0.20(Predicted)
• Flash Point: 366.202 °C
• PSA: 98.74000
• Density: 1.221 g/cm³
• LogP: 1.09970
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 361.20015635
• Heavy Atom Count: 26
• Complexity: 537

Purity/Quality:

98%,99%, ^*data from raw suppliers

Semagacestat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)NC(C)C(=O)NC1C2=CC=CC=C2CCN(C1=O)C)O
• Isomeric SMILES: C[C@@H](C(=O)N[C@H]1C2=CC=CC=C2CCN(C1=O)C)NC(=O)[C@H](C(C)C)O
• Recent ClinicalTrials: Effect of LY450139 on the Long Term Progression of Alzheimer's Disease
• Recent EU Clinical Trials: Open-Label Extension for Alzheimer’s Disease Patients Who Complete One of Two Semagacestat Phase 3 Double-Blind Studies (H6L-MC-LFAN or H6L-MC-LFBC)
• Uses: Semagacestat is an inhibitor of the γ-secretase enzyme. γ-Secretase enzyme is pivotal in the generation of β-amyloid (Aβ), a neurotoxic endogenous peptide believed to be involved in the pathogenesis o f Alzheimer's disease (AD). Semagacestat is an inhibitor of the γ-secretase enzyme. γ-Secretase enzyme is pivotal in the generation of β-amyloid (Aβ), a neurotoxic endogenous peptide believed to be involved in the pathogenesis of Alzheimer''s disease (AD).

Technology Process of Semagacestat

There total 3 articles about Semagacestat 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: 83.0%

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) + CH4O3S*C14H19N3O2 (960589-84-8) → Semagacestat (425386-60-3)

Guidance literature:

(S)-2-Hydroxy-3-methylbutanoic acid; CH₄O₃S*C₁₄H₁₉N₃O₂; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

In water; acetone;

DOI:10.1055/s-0029-1216813

Reference yield:

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) + C14H19N3O2*ClH (960589-85-9) → Semagacestat (425386-60-3)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethanol; water; at 0 - 40 ℃; for 4.5h; optical yield given as %ee; Large scale reaction;

DOI:10.1021/op800240d

Reference yield:

C22H35N3O4Si → Semagacestat (425386-60-3)

Guidance literature:

With water;

DOI:10.1055/s-0029-1216813

upstream raw materials:

(S)-2-Hydroxy-3-methylbutanoic acid

C₁₄H₁₉N₃O₂*ClH

CH₄O₃S*C₁₄H₁₉N₃O₂

Refernces

• 1、 Boini, Sathish K.,Vaid, Radhe K.,Moder, Kenneth P.,Mitchell, David. "Synthesis of a substituted benzazepin-2-one dihydrate". scheme or table. p. 1983 - 1986. Retrieved 2010/01/13.