1201903-02-7

Basic information

• Product Name: Ixazomib Impurity 1
• Synonyms: Ixazomib Impurity 1;2,5-dichloro-N-(2-(((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)amino)-2-oxoethyl)benzamide
• CAS NO: 1201903-02-7
• Molecular Formula: C₂₄H₃₃BCl₂N₂O₄
• Molecular Weight: 495.24682
• Mol File: 1201903-02-7.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Dichloromethane; Chloroform; Methanol; Ethyl Acetate; DMSO
• CAS DataBase Reference: Ixazomib Impurity 1(CAS DataBase Reference)
• NIST Chemistry Reference: Ixazomib Impurity 1(1201903-02-7)
• EPA Substance Registry System: Ixazomib Impurity 1(1201903-02-7)

Safety Data

• Hazardous Substances Data: 1201903-02-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ixazomib Impurity 1 is used as an intermediate in the synthesis of Ixazomib, an anticancer agent, for its role in preventing cell growth in solid tumors.
Ixazomib Impurity 1 is used as a component in the development of proteasome inhibitors for the treatment of multiple myeloma patients, due to its contribution to the overall synthesis process of Ixazomib.
Additionally, Ixazomib Impurity 1 plays a role in the study and understanding of the potential neurotoxic effects of Ixazomib, as it is an integral part of the synthesis pathway.

Upstream product

• 1310383-72-2 (aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate 
• 667403-46-5 2-[(2,5-dichlorobenzoyl)amino]acetic acid 
• 179324-86-8 (1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]decan-4-yl]butan-1-amine 
• 84110-34-9 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole 
• 85167-14-2 (3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole 
• 779357-85-6 (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride 
• 18680-27-8 pinanediol 
• 50-79-3 2,5-dichlorobenzoic acid 
• 2905-61-5 2,5-dichlorobenzoyl chloride 

Downstream Products

• 1201903-03-8 Ν,Ν',Ν''-[boroxin-2,4,6-triyltris[[(1R)-3-methylbutane-1,1-diyl]imino(2-oxoethane-2,1-diyl)]]tris(2,5-dichlorobenzamide) 
• 1239908-20-3 2,2’-{2-[(1R)-1-({[(2,5-dichlorobenzoyl)amino]acetyl}amino)-3-methylbutyl]-5-oxo-1,3,2-dioxaborolane-4,4-diyl}diacetic acid 
• 1072833-77-2 Ixazomib 

Relevant articles and documents

Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids

Boronic acids are an increasingly important compound class for many applications, including C-C bond formation reactions, medicinal chemistry, and diagnostics. The deprotection of boronic ester intermediates is frequently a problematic and inefficient step in boronic acid syntheses. We describe an approach that highly facilitates this transformation by leveraging the volatility of methylboronic acid and its diol esters. The method is performed under mild conditions, provides high yields, and eliminates cumbersome and problematic purification steps.

Synthetic process research of ixazomib

The invention discloses a synthesis method of ixazomib. The yield and the purity of a target product can be greatly increased with the method.

NOVEL CRYSTALLINE FORMS OF IXAZOMIB CITRATE AND ITS PROCESS FOR PREPARATION THEREOF

The present invention related to novel crystalline forms of Ixazomib citrate of formula-I and its process for preparation thereof. The chemical structure of said compound represented by the following formula-I. This invention also provides a process for the preparation of Ixazomib citrate of formula-I and also its solid dispersions.

A PROCESS FOR THE PREPARATION OF IXAZOMIB CITRATE

The present invention relates to a process for the preparation of compound of formula (I), wherein, R1 and R2 are each independently hydroxy, alkoxy, aryloxy, or aralkoxy; or R1 and R2 together form a moiety derived from an alpha-hydroxy carboxylic acid compound or a beta-hydroxy carboxylic acid compound, wherein the atom attached to boron in each case is an oxygen atom; or R1 and R2 together form the boronate esters of boronic acid.

Preparation process method for boron-containing compound

The invention discloses a preparation method for a boron-containing compound MLN2238. The method for preparing the MLN2238, disclosed by the invention, comprises the steps of adopting a solid compound intermediate II, which is stable in properties and can be subjected to recrystallization and purification, as an intermediate node for quality control, carrying out recrystallization or pulping purification on the intermediate, and then, carrying out a next-step reaction, thereby obtaining the boron-containing compound MLN2238 with relatively high purity. The synthesis process route is free of special requirements on production equipment, the reaction conditions are mild, and all the raw materials are all marketable products, so that the process route is very applicable to industrial production.

Deuterated dipeptide boric acids or esters thereof, and synthetic methods and uses of the compounds

Deuterated dipeptide boric acids or esters thereof, or crystal forms thereof, or pharmaceutically acceptable hydrates or solvates thereof are disclosed. The general structure of the compounds is shown as a formula (a) in the specification, wherein R1, R2, R3, R4, R5 and R6 are independently selected from hydrogen, deuterium or halogens, or C1-C4 alkyl one or a plurality of or all hydrogen atoms of which are deuterated; and at least one of the R1, the R2, the R3, the R4, the R5 and the R6 is deuterated or deuterium. The compounds can effectively inhibit proteasomes and effectively treat or prevent cancer, cardiovascular disease, inflammation, immune disease, nephropathy, vasculogenesis or prostate disease.

Preparation method of boron-containing compound

The invention discloses a preparation method of boron-containing compound MLN9708. The preparation method of the MLN9708 includes use of a raw material IV convenient and easy to obtain for synthesis of an intermediate II capable of purification by recrystallization and then use of citric acid for boric acid ester exchange reaction to obtain the boron-containing compound MLN9708. The synthetic process route has no special requirement on production equipment, the reaction condition is mild, all the raw materials are commercially available products, and the process route is very suitable for industrial production.

A PROCESS OF PREPARING IXAZOMIB CITRATE

A novel production process of Ixazomib citrate of formula I, wherein the boroester of formula VII is hydrolyzed with boric acid, followed by esterification with citric acid. The hydrolysis with boric acid and esterification with citric acid are performed in a single step. The usual amount of boric acid varies between 1 to 3-fold the amount of the compound of formula VII (molar ratio). In a preferred embodiment the acid is used in a slight excess, i.e. 1.05 to 1.3-fold, optimally 1.1 -fold the molar amount of the compound of formula VII.

BORONATE ESTER COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF

The present invention provides novel compounds useful as proteasome inhibitors. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various diseases.