Sitagliptin DeaMino IMpurity 1

Base Information

• Chemical Name: Sitagliptin DeaMino IMpurity 1
• CAS No.: 1253056-18-6
• Molecular Formula: C₁₆H₁₂F₆N₄O
• Molecular Weight: 390.288
• Mol file: 1253056-18-6.mol

Synonyms:

Chemical Property of Sitagliptin DeaMino IMpurity 1

Chemical Property:

• Boiling Point: 517.5±60.0 °C(Predicted)
• PKA: -0.06±0.20(Predicted)
• Density: 1.52±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol

Purity/Quality:

99%+, ^*data from raw suppliers

3-Desamino-2,3-dehydroSitagliptin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Desamino-2,3-dehydro Sitagliptin is an impurity of Sitagliptin (S491000); a trizolopyrazine dipeptidyl peptidase IV inhibitor. Sitagliptin has recently been approved for the therapy of type II diabetes.

Technology Process of Sitagliptin DeaMino IMpurity 1

There total 2 articles about Sitagliptin DeaMino IMpurity 1 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:

(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) → (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) + C16H12F6N4O (1253056-18-6)

Guidance literature:

With sodium acetate; acetic anhydride; In toluene; for 6h; Overall yield = 85 g; Reflux;

Reference yield:

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) → C16H12F6N4O (1253056-18-6)

Guidance literature:

With palladium on activated charcoal; hydrogen; acetic anhydride; acetic acid;

Reference yield:

C16H12F6N4O (1253056-18-6) → (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 phosphate

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / methanol / 24 h / 20 °C

2: phosphoric acid / isopropyl alcohol / 20 °C

With phosphoric acid; acetic acid; In methanol; isopropyl alcohol;

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

Refernces