MLN9708

Base Information

• Chemical Name: MLN9708
• CAS No.: 1201902-80-8
• Molecular Formula: C20H23BCl2N2O9
• Molecular Weight: 517.128
• Hs Code.: 29329990
• Mol file: 1201902-80-8.mol

Synonyms:4-Carboxy-2-[(1R)-1-[[2-[(2,5-dichlorobenzoyl)amino]acetyl]amino]-3-methylbutyl]-6-oxo-1,3,2-dioxaborinane-4-acetic acid; Ixazomib

Chemical Property of MLN9708

Chemical Property:

• PKA: 1.92±0.20(Predicted)
• PSA: 168.33000
• Density: 1.47
• LogP: 2.74480
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)

Purity/Quality:

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

MLN-9708 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: Ixazomib citrate is a proteasome inhibitor prodrug for the treatment of multiple myeloma in patients who have received at least one prior therapy in combination with lenalidomide and dexamethasone. The drug was developed by Takeda and reversibly inhibits the protein proteasome subunit β type-5, which is part of the 20S proteasome complex. Ixazomib citrate (XXIV) is hydrolyzed quickly in vivo to give the biologically active compound ixazomib, which presumably is the corresponding boronic acid variant of XXIV.
• Uses: MLN-9708 is a novel proteasome?inhibitor.
• Clinical Use: Highly selective and reversible proteasome inhibitor: Treatment of multiple myeloma in combination with lenalidomide and dexamethasone
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: concentration reduced by rifampicin - avoid. Antidepressants: concentration possibly reduced by St John’s wort - avoid. Antiepileptics: concentration possibly reduced by carbamazepine, fosphenytoin and phenytoin - avoid. Antipsychotics: increased risk of agranulocytosis with clozapine - avoid.

Technology Process of MLN9708

There total 7 articles about MLN9708 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: 98.0%

Ν,Ν',Ν''-[boroxin-2,4,6-triyltris[[(1R)-3-methylbutane-1,1-diyl]imino(2-oxoethane-2,1-diyl)]]tris(2,5-dichlorobenzamide) (1201903-03-8) + citric acid (77-92-9,906507-37-7) → 4-(carboxymethyl)-2-((R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutyl)-6-oxo-1,3,2-dioxaborinane-4-carboxylic acid (1201902-80-8)

Guidance literature:

In ethyl acetate; at 25 - 74 ℃; Product distribution / selectivity;

Reference yield: 94.0%

Ixazomib (1072833-77-2) + citric acid (77-92-9,906507-37-7) → 4-(carboxymethyl)-2-((R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutyl)-6-oxo-1,3,2-dioxaborinane-4-carboxylic acid (1201902-80-8)

Guidance literature:

In ethyl acetate; at 60 - 74 ℃; for 3h;

Reference yield:

C14H17BCl2F3N2O2(1-)*K(1+) + citric acid (77-92-9,906507-37-7) → 4-(carboxymethyl)-2-((R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutyl)-6-oxo-1,3,2-dioxaborinane-4-carboxylic acid (1201902-80-8) + C19H21BCl2N2O9

Guidance literature:

C₁₄H₁₇BCl₂F₃N₂O₂^(1-)*K⁽¹⁺⁾; citric acid; With triethylamine; In ethyl acetate; acetonitrile; at 20 ℃; for 0.5h;

With chloro-trimethyl-silane; In ethyl acetate; acetonitrile; at 20 ℃; for 8h; Concentration;

upstream raw materials:

Ν,Ν',Ν''-[boroxin-2,4,6-triyltris[[(1R)-3-methylbutane-1,1-diyl]imino(2-oxoethane-2,1-diyl)]]tris(2,5-dichlorobenzamide)

citric acid

Ixazomib

2,5-dichlorobenzoic acid

Refernces

• 1、 -. "Boron-containing intermediate and application of same to medical industry". Paragraph 0056; 0057; 0058; 0067; 0071; 0076; 0081. . Retrieved 2017/08/28.