Sitagliptin Defuoro IMpurity 5

Base Information

• Chemical Name: Sitagliptin Defuoro IMpurity 5
• CAS No.: 486460-31-5
• Molecular Formula: C16H16F5N5O
• Molecular Weight: 389.32
• Mol file: 486460-31-5.mol

Synonyms:

Chemical Property of Sitagliptin Defuoro IMpurity 5

Chemical Property:

• Boiling Point: 530.3±60.0 °C(Predicted)
• PKA: 7.60±0.10(Predicted)
• Density: 1.56±0.1 g/cm3(Predicted)

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Sitagliptin Defuoro IMpurity 5

There total 11 articles about Sitagliptin Defuoro IMpurity 5 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: 85.0%

7-[(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine (486460-22-4) → 7-[(3R)-3-amino-4-(2,5-difluorophenyl)butanoyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine (486460-31-5)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 1h;

DOI:10.1021/jm0493156

Reference yield:

3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine (486460-20-2) → 7-[(3R)-3-amino-4-(2,5-difluorophenyl)butanoyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine (486460-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / H₂ / Pd/C / ethanol / 18 h / 20 °C / atmospheric pressure

2: 92 percent / HOBT; EDC / dimethylformamide / 16 h / 20 °C

3: 85 percent / HCl / methanol / 1 h / 20 °C

With hydrogenchloride; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm0493156

Reference yield:

trifluoro-acetic acid N'-pyrazin-2-yl-hydrazide; compound with trifluoro-acetic acid → 7-[(3R)-3-amino-4-(2,5-difluorophenyl)butanoyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine (486460-31-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 16.21 g / polyphosphoric acid / 18 h / 140 °C

2: 86 percent / H₂ / Pd/C / ethanol / 18 h / 20 °C / atmospheric pressure

3: 92 percent / HOBT; EDC / dimethylformamide / 16 h / 20 °C

4: 85 percent / HCl / methanol / 1 h / 20 °C

With hydrogenchloride; PPA; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm0493156

upstream raw materials:

7-[(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine

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

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid

2-(bromomethyl)-1,4-difluorobenzene

Refernces

• 1、 Kim, Dooseop,Wang, Liping,Beconi, Maria,Eiermann, George J.,Fisher, Michael H.,He, Huaibing,Hickey, Gerard J.,Kowalchick, Jennifer E.,Leiting, Barbara,Lyons, Kathryn,Marsilio, Frank,McCann, Margaret E.,Patel, Reshma A.,Petrov, Aleksandr,Scapin, Giovanna,Patel, Sangita B.,Roy, Ranabir Sinha,Wu, Joseph K.,Wyvratt, Matthew J.,Zhang, Bei B.,Zhu, Lan,Thornberry, Nancy A.,Weber, Ann E.. "(2R)-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: A potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes". . p. 141 - 151. Retrieved 2007/10/03.