1169707-30-5

Basic information

• Product Name: (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
• Synonyms: (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
• CAS NO: 1169707-30-5
• Molecular Formula: C₂₄H₂₃F₆N₅O
• Molecular Weight: 511.4627392
• Mol File: 1169707-30-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 612.2±65.0 °C(Predicted)
• Appearance: /
• Density: 1.42
• PKA: 7?+-.0.38(Predicted)
• CAS DataBase Reference: (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(CAS DataBase Reference)
• NIST Chemistry Reference: (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(1169707-30-5)
• EPA Substance Registry System: (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(1169707-30-5)

Safety Data

• Hazardous Substances Data: 1169707-30-5(Hazardous Substances Data)

Usage

General Description

(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 a chemical compound with a complex structure that includes fluoro-substituted aromatic rings and a pyrazine ring. It is composed of a butanone core with an amino group linked to a phenylethyl group and a trifluoromethyl-substituted pyrazino-triazole ring. (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 be of interest for its potential pharmacological properties, due to its structural features and potential interactions with biological targets. However, further research is necessary to fully understand its potential uses and mechanisms of action.

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

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

Downstream Products

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

Relevant articles and documents

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.

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.]