865758-95-8

Basic information

• Product Name: 2-[(6-CHLORO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)METHYL]BENZONITRILE
• Synonyms: 2-[(6-CHLORO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)METHYL]BENZONITRILE;2-((6-Chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile;2-[(6-Chloro-3,4-dihydro-2,4-dioxo-1(2H)-pyriMidinyl)Methyl]-benzonitrile;Agger coluMn dean interMediates;Benzonitrile, 2-[(6-chloro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)methyl]-;Alogliptin Related Compound 27
• CAS NO: 865758-95-8
• Molecular Formula: C₁₂H₈ClN₃O₂
• Molecular Weight: 261.6638
• Mol File: 865758-95-8.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Density: 1.48
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• PKA: 8.11±0.40(Predicted)
• CAS DataBase Reference: 2-[(6-CHLORO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)METHYL]BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(6-CHLORO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)METHYL]BENZONITRILE(865758-95-8)
• EPA Substance Registry System: 2-[(6-CHLORO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)METHYL]BENZONITRILE(865758-95-8)

Safety Data

• Hazardous Substances Data: 865758-95-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 865758-95-8 differently. You can refer to the following data:
1. Alogliptin (A575425) intermediate.
2. 2-((6-Chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile is used as a reactant/ intermediate in discovery of Alogliptin (A575425), which is an antidiabetic agent.

Upstream product

• 22115-41-9 2-(bromomethyl)benzonitrile 
• 4270-27-3 6-chlorouracil 

Downstream Products

• 865758-96-9 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile 

Relevant articles and documents

Synthesis process of alogliptin benzoate

The invention discloses a synthesis process of alogliptin benzoate. The synthesis process comprises the following steps: 1, preparing an initial raw material 6-chlorouracil; 2, preparing 2-((6-chlorine-2, 4-dioxo-3, 4-dihydro-2H-pyrimidine-1-radical)methyl)cyanophenyl; 3, preparing 2-[(6-chlorine-3, 4-dihydro-3-methyl-2, 4-dioxo-1(2H)-pyrimidinyl)methyl]benzonitrile; 4, preparing alogliptin; 5, preparing alogliptin benzoate. According to the invention, the alogliptin benzoate is synthesized by taking cheap and easily available 6-chlorouracil, alpha bromo-o-methylbenzonitrile and (R)-3-aminopiperidine as raw materials through reactions such as alkylation, methylation, affinity substitution, salification and the like; according to the synthetic route, raw materials are cheap and easy to obtain, the synthetic cost is reduced, all steps are classic reactions, and synthesis improvement is easy; the improved process is low in raw material cost, simple to operate, mild in reaction condition,simple in post-treatment and suitable for industrial production.

A preparation method of the midbody [...] (by machine translation)

The invention discloses a method of preparing intermediates of [...], including: will be 10.0 g raw material compound 1 is added to the 100 ml volume ratio of 1:1 of in the mixed solvent of DMSO/DMF, stirred at room temperature, after dissolving, adding 2

Discovery of highly potent DPP-4 inhibitors by hybrid compound design based on linagliptin and alogliptin

Highly potent DPP-4 inhibitors have been identified by hybrid compound design based on linagliptin and alogliptin. The most promising compound 2h (IC50 = 0.31 nM) exhibited 8.5-fold and 2.5-fold more potent activity than that of alogliptin (IC50 = 2.63 nM) and linagliptin (IC 50 = 0.77 nM), respectively. Compound 2h had a good inhibition selectivity for DPP-4 over DPP-8/9 and thus was selected for further biological evaluation, including oral glucose tolerance, plasma DPP-4 inhibitory activity, pharmacokinetic profile, acute toxicity and hERG inhibition. The assay results showed that 2h displayed significant in vivo glucose-lowering effect and low risk of toxicity. Further studies are expected to confirm 2h as a potential drug candidate for the treatment of type 2 diabetes.