Avagacestat (BMS-708163)

Base Information

• Chemical Name: Avagacestat (BMS-708163)
• CAS No.: 1146699-66-2
• Molecular Formula: C20H17ClF4N4O4S
• Molecular Weight: 520.892
• Mol file: 1146699-66-2.mol

Synonyms:(2R)-2-[N-[(4-Chlorophenyl)sulfonyl]-N-[[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]amino]-5,5,5-trifluoropentanamide;(2R)-2-[(4-chlorophenyl)sulfonyl-[[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]amino]-5,5,5-trifluoro-pentanamide;

Chemical Property of Avagacestat (BMS-708163)

Chemical Property:

• Appearance/Colour: White to off-white solid
• Boiling Point: 652.258 °C at 760 mmHg
• Flash Point: 348.273 °C
• PSA: 127.77000
• Density: 1.488 g/cm³
• LogP: 5.69750
• Solubility.: insoluble in H2O; ≥177.6 mg/mL in DMSO; ≥47.6 mg/mL in EtOH with ultrasonic

Purity/Quality:

98% min ^*data from raw suppliers

BMS 708163 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Avagacestat acts as a γ-secretase inhibitor allowing for treatment of ALzheimer’s disease. On addition it has seen uses targeting embryonic signaling pathways, which control stem cell and cellular development process in cancer therapy.

Technology Process of Avagacestat (BMS-708163)

There total 6 articles about Avagacestat (BMS-708163) 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: 90.8%

C14H14F4N4O2 + 4-chlorobenzenesulfonyl chloride (98-60-2) → avagacestat (1146699-66-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; Heating;

Reference yield: 90.0%

(R)-2-(4-chloro-N-(2-fluoro-4-(N'-hydroxycarbamimidoyl)benzyl)phenylsulfonamido)-5,5,5-trifluoropentanamide (1146699-70-8) + orthoformic acid triethyl ester (122-51-0) → avagacestat (1146699-66-2)

Guidance literature:

With trifluoroacetic acid; In acetonitrile; at 40 - 50 ℃; Product distribution / selectivity;

Reference yield: 50.0%

3-(4-(bromomethyl)-3-fluorophenyl)-1,2,4-oxadiazole (1146699-64-0) + (R)-2-(4-chlorophenylsulfonamido)-5,5,5-trifluoropentanamide (1146699-67-3) → avagacestat (1146699-66-2)

Guidance literature:

With hydroxylamine; tetra-(n-butyl)ammonium iodide; caesium carbonate; In acetonitrile; at 15 - 35 ℃; Product distribution / selectivity;

upstream raw materials:

(R)-2-(4-chloro-N-(2-fluoro-4-(N'-hydroxycarbamimidoyl)benzyl)phenylsulfonamido)-5,5,5-trifluoropentanamide

orthoformic acid triethyl ester

3-(4-(bromomethyl)-3-fluorophenyl)-1,2,4-oxadiazole

(R)-2-(4-chlorophenylsulfonamido)-5,5,5-trifluoropentanamide

Refernces

• 1、 Gillman, Kevin W.,Starrett Jr., John E.,Parker, Michael F.,Xie, Kai,Bronson, Joanne J.,Marcin, Lawrence R.,McElhone, Kate E.,Bergstrom, Carl P.,Mate, Robert A.,Williams, Richard,Meredith, Jere E.,Burton, Catherine R.,Barten, Donna M.,Toyn, Jeremy H.,Roberts, Susan B.,Lentz, Kimberley A.,Houston, John G.,Zaczek, Robert,Albright, Charles F.,Decicco, Carl P.,MacOr, John E.,Olson, Richard E.. "Discovery and evaluation of BMS-708163, a potent, selective and orally bioavailable γ-secretase inhibitor". scheme or table. p. 120 - 124. Retrieved 2010/12/20.