1108732-05-3

Basic information

• Product Name: 2-((6-(3-aMinopiperidin-1-yl)-3-Methyl-2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)Methyl)benzonitrile
• Synonyms: 2-((6-(3-aMinopiperidin-1-yl)-3-Methyl-2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)Methyl)benzonitrile;Alogliptin benzoate impurity A
• CAS NO: 1108732-05-3
• Molecular Formula: C18H21N5O2
• Molecular Weight: 339.39164
• Mol File: 1108732-05-3.mol
• Article Data: 30

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-((6-(3-aMinopiperidin-1-yl)-3-Methyl-2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)Methyl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((6-(3-aMinopiperidin-1-yl)-3-Methyl-2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)Methyl)benzonitrile(1108732-05-3)
• EPA Substance Registry System: 2-((6-(3-aMinopiperidin-1-yl)-3-Methyl-2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)Methyl)benzonitrile(1108732-05-3)

Safety Data

• Hazardous Substances Data: 1108732-05-3(Hazardous Substances Data)

Usage

General Description

2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile is a chemical compound with a complex molecular structure. It contains a benzene ring and a nitrile group, as well as a piperidine and a pyrimidine ring. The compound also contains a methyl group and an amino group, adding to its complexity. This chemical may have potential uses in pharmaceutical research or as a building block in the synthesis of other compounds. Further research and analysis may be required to fully understand its properties and potential applications.

Upstream product

• 309956-78-3 (R)-piperidin-3-ylcarbamic acid tert-butyl ester 
• 865758-96-9 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile 
• 4318-56-3 3-methyl-6-chlorouracil 
• 22115-41-9 2-(bromomethyl)benzonitrile 
• 334618-23-4 3-(R)-aminopiperidine dihydrochloride 
• 7032-11-3 1,4,5,6-tetrahydropyridine-3-carboxamide 
• 98-92-0 nicotinamide 
• 1381795-31-8 3-(R)-piperidinyl phthalimide hydrochloride 
• 344957-25-1 2-(aminomethyl)benzonitrile 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 127294-73-9 (R)-piperidin-3-ylamine 
• 1246610-74-1 2-[[6-[(3R)-3-tert-butoxycarbonylamino-1-piperidinyl]-3,4-dihydro-2,4-dioxo-3-methyl-1(2H)-pyrimidinyl]methyl]benzonitrile 
• 612-13-5 2-cyanobenzyl chloride 
• 865758-95-8 2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile 

Downstream Products

• 850649-62-6 C₇H₆O₂*C₁₈H₂₁N₅O₂ 
• 1638544-64-5 alogliptin benzoate 

Relevant articles and documents

Development and Scale-Up of an Asymmetric Synthesis Process for Alogliptin

Alogliptin (1) benzoate is a potent, highly selective inhibitor of serine protease dipeptidyl-peptidase IV, approved by US FDA for the treatment of type 2 diabetes. Herein, we report a more cost-effective process that includes ruthenium-catalyzed asymmetric hydrogenation followed by Hofmann rearrangement of 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile (10) to introduce a chiral amino moiety at a late stage. Use of an inexpensive and readily available nicotinamide (6) for a chiral aminopiperidine core and iodobenzene diacetate (PIDA) under mild and specific conditions allowed us to access 1 with excellent total yield and comparable quality to that manufactured by the original process.

3, 4-dihydropyrimidine benzonitrile derivative as well as preparation method and application thereof

The invention provides a 3, 4-dihydropyrimidine benzonitrile derivative as well as a preparation method and application thereof. The invention discloses a structure of a specific impurity (RRT is an impurity of 1.22) generated in the process of preparing alogliptin benzoate by adopting the route of the original research patent for the first time. The series of impurities have a warning structure,and the content of the impurities in the alogliptin benzoate finished product needs to be detected according to related limits of the genetically toxic impurities. The invention further provides a preparation and purification method of the high-purity compound shown in the formula (A) and a detection method of the content of the impurity compound in the alogliptin benzoate medicine, and thereforequality control over the alogliptin benzoate medicine is achieved.

Preparation method of alogliptin benzoate

The invention discloses a preparation method of alogliptin benzoate. Main starting materials of the preparation method are 6-chloro-3-methyluracil, o-cyanobenzyl bromide, (R)-3-Boc-aminopiperidine andbenzoic acid. According to the method, all indexes meet the specification, meanwhile, dangerous reagents such as sodium hydride and highly toxic methyl iodide are prevented from being used in the reaction process, the requirement for the operation process is not strict, and water-free and oxygen-free conditions are not needed; a high-boiling-point mixed solvent is not used in the reaction, and the solvent is easy to recycle; the selected starting materials are available in the market and easy to obtain, and large-scale production is facilitated; in addition, starting materials or intermediates in the synthetic route are good in stability and convenient to store and control, and genotoxic impurities are avoided in the reaction process; and the synthesis process is environment-friendly.