tert-Butyl 3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate

Base Information

• Chemical Name: tert-Butyl 3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate
• CAS No.: 877402-43-2
• Molecular Formula: C11H15 F3 N4 O2
• Molecular Weight: 292.26
• Mol file: 877402-43-2.mol

Synonyms:tert-Butyl3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate

Chemical Property of tert-Butyl 3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate

Chemical Property:

• Boiling Point: 356.9±52.0 °C(Predicted)
• PKA: 0.25±0.20(Predicted)
• PSA: 60.25000
• Density: 1.43±0.1 g/cm3(Predicted)
• LogP: 1.98550
• Storage Temp.: -20°C Freezer
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

98% ^*data from raw suppliers

tert-Butyl3-(Trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-Butyl 3-(Trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate is an intermediate in the synthesis of Sitagliptin Triazecine Analog (S491015). Sitagliptin Triazecine Analog is related to the family of Sitagliptin compounds which has recently been approved for the therapy of type II diabetes.

Technology Process of tert-Butyl 3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate

There total 3 articles about tert-Butyl 3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

di-tert-butyl dicarbonate (24424-99-5) + 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (486460-21-3) → tert-butyl 3-(trifluoromethyl)-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate (877402-43-2)

Guidance literature:

In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/jm070330v

Reference yield:

3-bromo-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylic acid tert-butyl ester (723286-80-4) + (trifluoromethyl)trimethylsilane (81290-20-2) → tert-butyl 3-(trifluoromethyl)-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate (877402-43-2)

Guidance literature:

With 4,4'-dimethyl-2,2'-bipyridines; (1,10-phenanthroline)bis(5-methyl-2-(4-fluoro)phenylpyridine-N,C)iridium(III) hexafluorophosphate; sodium acetate; N-(adamantan-1-yl)-1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilan-2-amine; copper(I) bromide; In acetonitrile; Irradiation;

DOI:10.1021/jacs.0c09977

Reference yield:

→ tert-butyl 3-(trifluoromethyl)-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate (877402-43-2)

Guidance literature:

upstream raw materials:

di-tert-butyl dicarbonate

3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

3-bromo-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylic acid tert-butyl ester

(trifluoromethyl)trimethylsilane

Downstream raw materials:

C₂₀H₁₉F₉N₄O₂

C₁₈H₂₀F₄N₄O₂

Refernces

• 1、 Kim, Dooseop,Kowalchick, Jennifer E.,Brockunier, Linda L.,Parmee, Emma R.,Eiermann, George J.,Fisher, Michael H.,He, Huaibing,Leiting, Barbara,Lyons, Kathryn,Scapin, Giovanna,Patel, Sangita B.,Petrov, Aleksandr,Pryor, Kelly Ann D.,Roy, Ranabir Sinha,Wu, Joseph K.,Zhang, Xiaoping,Wyvratt, Matthew J.,Zhang, Bei B.,Zhu, Lan,Thornberry, Nancy A.,Weber, Ann E.. "Discovery of potent and selective dipeptidyl peptidase IV inhibitors derived from β-aminoamides bearing subsituted triazolopiperazines". . p. 589 - 602. Retrieved 2008/09/17.