Sitagliptin IMpurity

Base Information

• Chemical Name: Sitagliptin IMpurity
• CAS No.: 1675201-14-5
• Molecular Formula: C₁₆H₁₂F₆N₄O
• Molecular Weight: 390.288
• Mol file: 1675201-14-5.mol

Synonyms:

Chemical Property of Sitagliptin IMpurity

Chemical Property:

• Melting Point: 113-115°C
• Boiling Point: 504.1±60.0 °C(Predicted)
• PKA: -0.03±0.20(Predicted)
• Density: 1.52±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1-[5,6-Dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-3-buten-1-one is a derivative of Sitagliptin(S491000) which is a trizolopyrazine dipeptidyl peptidase IV inhibitor. Sitagliptin has recently been approved for the therapy of type II diabetes.

Technology Process of Sitagliptin IMpurity

There total 5 articles about Sitagliptin IMpurity 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: 91.0%

sitagliptin (486460-32-6,823817-55-6) → (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 (1675201-14-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 120 ℃; for 12h; Solvent; Temperature; Reagent/catalyst;

Reference yield: 87.2%

C10H7F3O2 + 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride (762240-92-6) → (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 (1675201-14-5)

Guidance literature:

C₁₀H₇F₃O₂; With 1,1'-carbonyldiimidazole; In ethyl acetate; at 20 ℃; for 0.5h;

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride; With triethylamine; In ethyl acetate; at 20 ℃; Concentration;

Reference yield: 65.5%

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 (764667-65-4) → (3E)-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)but-3-en-1-one (1675201-14-5)

Guidance literature:

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; With dimethylsulfide borane complex; In methanol; at 20 ℃; for 0.416667h;

With methanesulfonyl chloride; triethylamine; In tetrahydrofuran; at 0 - 40 ℃; for 20h; Temperature; Reagent/catalyst; Solvent;

upstream raw materials:

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

(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

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

sitagliptin

Refernces

• 1、 -. "EXPEDIENT SYNTHESIS OF SITAGLIPTIN". . . Retrieved 2015/09/23.