823817-55-6

Basic information

• Product Name: Sitagliptin Impurity 1
• Synonyms: Sitagliptin Impurity 1
• CAS NO: 823817-55-6
• Molecular Formula: C16H15F6N5O
• Molecular Weight: 407.3136192
• Mol File: 823817-55-6.mol
• Article Data: 116

Chemical Properties

• Boiling Point: 529.9±60.0 °C(Predicted)
• Appearance: /
• Density: 1.61±0.1 g/cm3(Predicted)
• PKA: 7.20±0.10(Predicted)
• CAS DataBase Reference: Sitagliptin Impurity 1(CAS DataBase Reference)
• NIST Chemistry Reference: Sitagliptin Impurity 1(823817-55-6)
• EPA Substance Registry System: Sitagliptin Impurity 1(823817-55-6)

Safety Data

• Hazardous Substances Data: 823817-55-6(Hazardous Substances Data)

Usage

General Description

Sitagliptin Impurity 1 is a chemical substance that falls under the class of impurities associated with the drug sitagliptin, which is used to treat type 2 diabetes. This impurity is a potential by-product that may be present in sitagliptin formulations and needs to be closely monitored during the manufacturing process to ensure the purity and safety of the final drug product. It is crucial to identify and quantify the levels of Sitagliptin Impurity 1 to comply with regulatory standards and ensure the effectiveness and safety of the sitagliptin medication for patients. Proper control and management of this impurity are essential to guarantee the quality and efficacy of the sitagliptin drug.

Upstream product

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• 913623-45-7 1,2,4-trifluoro-5-(2-nitrovinyl)-benzene 
• 1240038-86-1 sitagliptin (R)-(-)mandelate 
• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 
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• 1152439-73-0 2,2-dimethyl-5-[2-(2,4,5-trifluorophenyl)acetyl]-[1,3]dioxane-4,6-dione 
• 767340-03-4 (Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one 
• 823817-56-7 (R/S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine 
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• 847445-81-2 dehydrositagliptin 
• 486460-21-3 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine 

Downstream Products

• 1190094-97-3 (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (-)dibenzolyl-L-tartaric acid salt 
• 1219440-27-3 (2S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (-)dibenzolyl-L-tartaric acid salt 
• 1219440-25-1 dibenzoyl-D-tartaric acid (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine 
• 1219440-26-2 dibenzoyl-D-tartaric acid (2S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine 
• 1219440-29-5 (S)-(+)-O-acetylmandelic acid (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine 
• 1219440-30-8 (S)-(+)-O-acetylmandelic acid (2S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine 

Relevant articles and documents

Two methods for the preparation of sitagliptin phosphate: Via chemical resolution and asymmetric hydrogenation

Two effective processes have been developed for the preparation of sitagliptin phosphate. The approach of chemical resolution obtained R-sitagliptin in five steps from commercially available starting materials using the inexpensive NaBH4 to reduce the enamine and then using (-)-di-p-toluoyl-l-tartaric acid to resolve racemates in 11% yield overall. The route successfully avoids the use of expensive noble metal as catalysts compared with traditional synthesis methods, resulting in greatly reduced costs and simplified synthetic routes. Other alternative asymmetric hydrogenation of β-ketomide routes for the synthesis of sitagliptin were found, two of the intermediates were synthesized for the first time. This journal is

Process method for improving yield and purity of sitagliptin

The invention provides a process method for improving yield and purity of sitagliptin, which comprises the following steps: mixing Boc sitagliptin as shown in a formula iii with solvent ester and acid, carrying out hydrolysis reaction at 0-50 DEG C, neutralizing with acid and alkali after the reaction is finished, and removing a water layer to obtain an organic layer containing sitagliptin as shown in a formula iv. The process method disclosed by the invention has the advantages that degradation of sitagliptin iv in reaction and post-treatment processes can be avoided, so that the yield and quality of sitagliptin iv are effectively improved.

Preparation method of chiral 4 - aryl - β β-amino acid derivative

Provided is a method for preparing a chiral 4-aryl-β-amino acid derivative. The preparation method comprises hydrogenating an enamine compound having a structure as shown in Formula III in an organic solvent in the presence of a catalyst containing a transition metal and BIBOPs. The preparation method of the present invention uses a small amount of a selected asymmetric catalyst, and has a simple operation, mild reaction conditions, a high yield, a high stereoselectivity, and better industrial application and economic values.