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

Description

Sitagliptin Impurity 1 is a chemical substance that is categorized as an impurity associated with the drug sitagliptin, which is utilized for the treatment of type 2 diabetes. This impurity is a potential by-product that may be present in sitagliptin formulations, necessitating stringent monitoring during the manufacturing process to ensure the purity, safety, and efficacy of the final drug product.

Uses

Sitagliptin Impurity 1 does not have direct applications in the pharmaceutical or other industries due to its classification as an impurity. However, its management and control are essential in the following areas:
Used in Pharmaceutical Manufacturing:
Sitagliptin Impurity 1 is managed as a critical quality attribute for ensuring the purity and safety of sitagliptin formulations. It is used as a parameter for monitoring and controlling the manufacturing process to comply with regulatory standards and to guarantee the effectiveness and safety of the sitagliptin medication for patients.
Used in Quality Control and Assurance:
Sitagliptin Impurity 1 is utilized as a benchmark for quality control and assurance in the pharmaceutical industry. It is used for identifying and quantifying the levels of impurities in sitagliptin drug products to ensure that they meet the required specifications and do not compromise the drug's therapeutic benefits or patient safety.
Used in Regulatory Compliance:
Sitagliptin Impurity 1 is monitored and controlled as part of the regulatory compliance process in the pharmaceutical industry. It is used to ensure that sitagliptin drug products adhere to the established guidelines and standards set by regulatory authorities, thereby maintaining the integrity and reliability of the medication.

Upstream product

• 1242069-63-1 (R)-benzyl (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-yl)carbamate 
• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 
• 144284-25-3 (2,4,5-trifluorophenyl)methanol 
• 764667-65-4 1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione 
• 762240-92-6 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride 
• 486460-21-3 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine 
• 654671-78-0 sitagliptin phosphate 
• 1169707-30-5 (3R)-3-[[(1R)-1-phenylethyl]amino]-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one 
• 769195-20-2 (3R)-3-[[(1S)-1-carboxamidophenylmethyl]amino]-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one 
• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 

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

IMPROVED PROCESS FOR PREPARATION OF SITAGLIPTIN

Provided herein is a process for the preparation of specific enantiomeric Sitagliptin with good chiral purity and higher yield using improved biocatalyst and by engineering an enzyme to mediate the efficient conversion of ketoamide to obtain enantiomerically pure Sitagliptin in presence of an amino group donor.

Synthesis method of sitagliptin free alkali

The invention belongs to the field of organic chemistry, and particularly discloses a synthesis method of sitagliptin free alkali. The synthesis method comprises the following specific steps: (1) dissolving (3R)-N-tert-butyloxycarbonyl-3-amino-4-(2,4,5-trifluorophenyl) butyric acid and organic alkali in an organic solvent, adding a phosphorus-containing condensing agent, then adding 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazol[4,3-alpha]pyrazine hydrochloride to prepare a compound represented by a formula (II); and (2) removing t-butyloxycarboryl from the compound shown in the formula II under the action of acid to obtain a compound I namely sitagliptin free alkali. The method is mild in process reaction condition, easy to control, short in reaction time, free of extraction, simple to operate and beneficial to industrial production, and the process cost is reduced; and the prepared compound shown in the formula I is high in yield, high in purity and free of heavy metal residues.

Synthesis method of sitagliptin free alkali and sitagliptin phosphate monohydrate

The invention relates to a synthesis method of sitagliptin free alkali and sitagliptin phosphate monohydrate. According to the method, dry HOBt is removed or changed into HOBt hydrate, a solvent DMF is removed in the process, and a simple solvent easy to recover is used in the production process, so that the production cost is reduced, and the reaction safety is improved. According to the invention, with the in-situ process from a compound represented by a formula 2 to a compound represented by a formula 6, the yield can be improved, the operation steps can be reduced, and the methanol or isopropanol IPA is replaced with other solvents so as to avoid the generation of impurities represented by a formula 7, a formula 8 and a formula 9, such that the product purity and the yield can be substantially improved, and the HPLC purity of the sitagliptin free alkali is more than 99%.