1246610-74-1

Basic information

• Product Name: 2-[[6-[(3R)-3-tert-butoxycarbonylamino-1-piperidinyl]-3,4-dihydro-2,4-dioxo-3-methyl-1(2H)-pyrimidinyl]methyl]benzonitrile
• Synonyms: 2-[[6-[(3R)-3-tert-butoxycarbonylamino-1-piperidinyl]-3,4-dihydro-2,4-dioxo-3-methyl-1(2H)-pyrimidinyl]methyl]benzonitrile;Alogliptin Related Compound 29
• CAS NO: 1246610-74-1
• Molecular Weight: 439.514
• Mol File: 1246610-74-1.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2-[[6-[(3R)-3-tert-butoxycarbonylamino-1-piperidinyl]-3,4-dihydro-2,4-dioxo-3-methyl-1(2H)-pyrimidinyl]methyl]benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[6-[(3R)-3-tert-butoxycarbonylamino-1-piperidinyl]-3,4-dihydro-2,4-dioxo-3-methyl-1(2H)-pyrimidinyl]methyl]benzonitrile(1246610-74-1)
• EPA Substance Registry System: 2-[[6-[(3R)-3-tert-butoxycarbonylamino-1-piperidinyl]-3,4-dihydro-2,4-dioxo-3-methyl-1(2H)-pyrimidinyl]methyl]benzonitrile(1246610-74-1)

Safety Data

• Hazardous Substances Data: 1246610-74-1(Hazardous Substances Data)

Usage

General Description

2-[[6-[(3R)-3-tert-butoxycarbonylamino-1-piperidinyl]-3,4-dihydro-2,4-dioxo-3-methyl-1(2H)-pyrimidinyl]methyl]benzonitrile, also known as TBOA, is a chemical compound used as a selective antagonist for excitatory amino acid transporters. It has been studied for its potential therapeutic applications in the treatment of neurological and psychiatric disorders, as well as in cancer treatment. TBOA is known to inhibit the reuptake of glutamate, an important neurotransmitter in the brain, and has been shown to have neuroprotective effects in certain animal models. Its precise mechanisms of action and potential side effects in humans are still under investigation, but it is considered a promising candidate for further drug development and research in the field of neuroscience and medicine.

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 
• 1246610-77-4 6-amino-1-(2-cyanobenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione 
• 1217656-59-1 (R)-piperidin-3-ylcarbamic acid tert-butyl ester hydrochloride 
• 4318-56-3 3-methyl-6-chlorouracil 
• 612-13-5 2-cyanobenzyl chloride 
• 22115-41-9 2-(bromomethyl)benzonitrile 
• 102-09-0 bis(phenyl) carbonate 
• 1246610-71-8 1-(2-cyanobenzyl)-3-methylurea 

Downstream Products

• 1246610-76-3 Alogliptin trifluoroacetate 
• 1638544-64-5 Alogliptin benzoate 
• 1246610-75-2 Alogliptin hydrochloride 
• 850649-61-5 alogliptin 

Relevant articles and documents

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.

A synthetic [...] intermediates

The present invention provides a method for synthesizing an intermediate V. The method comprises: (a) allowing a compound I and a compound II to react while being heated in a solvent under an alkaline condition to obtain an intermediate III; and (b) the intermediate III reacting with a compound IV in the solvent under the alkaline condition to obtain the intermediate V. The intermediate V can be used to synthesize alogliptin.

Alogliptin benzoate preparation method

The present invention provides an alogliptin benzoate preparation method, which comprises treating an intermediate IV reaction solution, and specifically comprises: heating the intermediate IV reaction solution to a temperature of 50-80 DEG C, adding a diluted alcohol while hot, cooling to a temperature of 0-40 DEG C to make the crystal be crystallized, adding water after a lot of the crystals are crystallized, carrying out stirring washing, filtering, and drying to obtain the intermediate IV. According to the present invention, the intermediate IV is prepared by using the one-pot method, a certain amount of the diluted alcohol is added at the high temperature, the saturated solution is formed after the cooling, and the cooling is continuously performed to crystallize, such that the crystal caking problem caused by the direct water precipitation is avoided, the intermediate IV crystal is uniformly dispersed, sticking on the wall and the agglomeration do not exist, the sticking onto the stirring slurry does not exist, the operation is convenient, and the method is suitable for industrial production.