1169707-30-5

Usage

Uses

Used in Pharmaceutical Industry:
(3R)-1-[5,6-Dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-3-[[(1R)-1-phenylethyl]amino]-4-(2,4,5-trifluorophenyl)-1-butanone is used as a potential pharmaceutical compound for its possible interactions with biological targets, which may lead to the development of new drugs or therapies. Further research is required to explore its pharmacological properties and mechanisms of action.
Used in Chemical Research:
In the field of chemical research, (3R)-1-[5,6-Dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-3-[[(1R)-1-phenylethyl]amino]-4-(2,4,5-trifluorophenyl)-1-butanone may serve as a starting material or a structural component in the synthesis of novel compounds with potential applications in various industries, including materials science, agrochemicals, and more. Its unique structure could provide insights into new chemical reactions and bonding mechanisms.

InChI:InChI=1S/C24H23F6N5O/c1-14(15-5-3-2-4-6-15)31-17(9-16-10-19(26)20(27)12-18(16)25)11-22(36)34-7-8-35-21(13-34)32-33-23(35)24(28,29)30/h2-6,10,12,14,17,31H,7-9,11,13H2,1H3/t14-,17-/m1/s1

Upstream product

• 1169707-29-2 (R,Z)-3-[(1-phenylethyl)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 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 
• 762240-92-6 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride 
• 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 
• 764667-64-3 5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 1345822-98-1 tert-butyl (3R)-3-[[(1R)-1-phenylethyl]amino]-4-(2,4,5-trifluorophenyl)butanoate maleate 
• 1345822-93-6 tert-butyl 3-[[(1R)-1-phenylethyl]amino]-4-(2,4,5-trifluorophenyl)-but-2-enoate 
• 1253056-18-6 C₁₆H₁₂F₆N₄O 
• 1253056-01-7 (R/S)-3-hydroxy-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one 
• 486460-21-3 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine 

Downstream Products

• 486460-32-6 sitagliptin 
• 654671-78-0 sitagliptin phosphate 
• 654671-77-9 sitagliptin phosphate monohydrate 
• 823817-55-6 (S)-Sitagliptin 

Relevant academic research and scientific papers

A west he row sandbank and intermediate preparation method

The invention relates to the field of medicament synthesis and especially relates to a preparation method of sitagliptin and an intermediate thereof. The preparation method of a compound show as formula III is as below: in the presence of a first organic solvent, a compound shown as formula I and a compound shown as formula II conduct reductive amination reaction under the action of a reducing agent and organic acid, so as to obtain the compound shown in formula III. The preparation method provided by the invention does not use precious metal as the catalyst, reduces the cost, simplifies the synthesis process, increases the yield, and improves the chemical purity and optical purity of sitagliptin. R represents methyl or carbamyl, and Ar represents phenyl, monosubstituted phenyl or polysubstituted phenyl.

METHOD FOR PREPARING INTERMEDIATE COMPOUND OF SITAGLIPTIN

The present invention provides a method for preparing an intermediate compound of sitagliptin represented by formula I. The preparation method comprises: dissolving a compound represented by formula II into an organic solvent; and under the catalysis of fatty acid and effect of chlorosilane, performing a reduction reaction of carbon-carbon double bonds, so as to obtain the intermediate compound of sitagliptin represented by formula I, R being methyl or formoxyl. The preparation method of the present invention avoids precious metal as a catalyst, and accordingly, the cost is low, the post-treatment is simple, the product has a high yield, chemical purity and optical purity, and de % is greater than 99.6%, and the preparation method can be used in synthesis of sitagliptin and is suitable for industrial production.

Practical, asymmetric route to sitagliptin and derivatives: Development and origin of diastereoselectivity

The development of a practical and scalable process for the asymmetric synthesis of sitagliptin is reported. Density functional theory calculations reveal that two noncovalent interactions are responsible for the high diastereoselection. The first is an intramolecular hydrogen bond between the enamide NH and the boryl mesylate S=O, consistent with MsOH being crucial for high selectivity. The second is a novel C-H···F interaction between the aryl C5-fluoride and the methyl of the mesylate ligand.

EXPEDIENT SYNTHESIS OF SITAGLIPTIN

Novel intermediates are disclosed as intermediates for preparation of a Sitagliptin. A novel synthetic method to prepare Sitagliptin using the said intermediates is also disclosed.

Practical and economical approach to synthesize sitagliptin

Economic syntheses of sitagliptin phosphate monohydrate, acknowledged as the first dipeptidyl peptidase 4 (DPP-4) inhibitor, have been achieved in an overall yield of 42.4% in four steps from 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. The key stereoselective reduction of this process was carried out by NaBH 4/HCOOH instead of expensive and toxic catalysts or ligands. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

PROCESS FOR THE PREPARATION OF CHIRAL BETA AMINO CARBOXAMIDE DERIVATIVES

The present invention provides a process for preparing a compound of formula (I), or a pharmaceutically acceptable salt thereof, having the R-configuration, of formula (IA), or S-configuration of formula (IB), selectively over the other enantiomer.

PREPARATION OF SITAGLIPTIN AND SALTS THEREOF

Processes for preparing sitagliptin and its pharmaceutically acceptable salts, and process intermediates.

PROCESSES FOR THE PREPARATION OF SITAGLIPTIN AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

There is provided salts and polymorphs of sitagliptin, processes for the preparation thereof, and pharmaceutical compositions comprising the same.