1253056-01-7

Basic information

• Product Name: (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
• Synonyms: (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
• CAS NO: 1253056-01-7
• Molecular Weight: 408.303
• Mol File: 1253056-01-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 542.2±60.0 °C(Predicted)
• Density: 1.61±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (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(CAS DataBase Reference)
• NIST Chemistry Reference: (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(1253056-01-7)
• EPA Substance Registry System: (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(1253056-01-7)

Safety Data

• Hazardous Substances Data: 1253056-01-7(Hazardous Substances Data)

Usage

Uses

1-[5,6-Dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-3-hydroxy-4-(2,4,5-trifluorophenyl)-1-butanone is an intermediate in the synthesis of 3-Desamino-2,3-dehydro Sitagliptin (D281985), which is an impurity of Sitagliptin (S491000); a trizolopyrazine dipeptidyl peptidase IV inhibitor. Sitagliptin has recently been approved for the therapy of type II diabetes.

Upstream product

• 847445-81-2 dehydrositagliptin 
• 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 
• 528-94-9 ammonium salicylate 
• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 

Downstream Products

• 1253056-02-8 3-bromo-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 
• 1169707-36-1 sitagliptin oxalate 
• 1675201-14-5 (Z/E)-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)but-3-en-1-one 
• 1253056-18-6 C₁₆H₁₂F₆N₄O 
• 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 
• 1456704-50-9 (2S)-2({(1S)-3-oxo-1-(2,4,5-trifluorobenzyl)-3-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-α]pyrazin-7(8H)-yl]propyl}amino)-2-phenylethanamide 
• 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 
• 1456704-47-4 (S)-3-(((R)-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)butan-1-one 
• 1433545-69-7 (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-yl p-toluenesulfonate 
• 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 
• 1433546-77-0 (R/S)-3-(benzylamino)-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 
• 1253056-14-2 (R/S)-3-(1,3-dioxoisoindolin-2-yl)-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 
• 1433546-02-1 (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-yl p-nitrobenzenesulfonate 

Relevant articles and documents

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.

PROCESS FOR THE PREPARATION OF SITAGLIPTIN AND ITS INTERMEDIATES

The present invention relates to novel and improved processes for the preparation of Sitagliptin compound of formula (1) and its intermediates.

Direct asymmetric reductive amination

(Chemical Equation Presented) Asymmetric reductive amination of β-keto amides catalyzed by the chiral catalyst Ru(OAc)2 ((R)-dm-segphos) produces unprotected β-amino amides with high yields and high enantioselectivities (94.7-99.5% ee). This "one-pot" methodology is general in substrate scope and has been successfully employed to produce sitagliptin with 99.5% ee and 91% assay yield. The excellent reaction efficiency is attributed to the remarkable tolerance to high concentrations of ammonium ion, the high chemoselectivity, and the high enantioselectivity (99.5% ee) of the Ru catalyst system.