4-Desfluoro N-boc sitagliptin

Base Information

• Chemical Name: 4-Desfluoro N-boc sitagliptin
• CAS No.: 486460-22-4
• Molecular Formula: C21H24F5N5O3
• Molecular Weight: 489.445
• UNII: 2SHC36P9ZT
• Mol file: 486460-22-4.mol

Synonyms:4-Desfluoro N-boc sitagliptin;UNII-2SHC36P9ZT;2SHC36P9ZT;486460-22-4;1,1-Dimethylethyl N-((1R)-1-((2,5-difluorophenyl)methyl)-3-(5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo(4,3-a)pyrazin-7(8H)-yl)-3-oxopropyl)carbamate;Carbamic acid, N-((1R)-1-((2,5-difluorophenyl)methyl)-3-(5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo(4,3-a)pyrazin-7(8H)-yl)-3-oxopropyl)-, 1,1-dimethylethyl ester;tert-Butyl (R)-(1-(2,5-difluorophenyl)-4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-(1,2,4)triazolo(4,3-a)pyrazin-7(8H)-yl)butan-2-yl)carbamate;SCHEMBL1509250;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;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-alpha]pyrazine

Chemical Property of 4-Desfluoro N-boc sitagliptin

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 489.17993045
• Heavy Atom Count: 34
• Complexity: 735

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=C(C=CC(=C1)F)F)CC(=O)N2CCN3C(=NN=C3C(F)(F)F)C2
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=C(C=CC(=C1)F)F)CC(=O)N2CCN3C(=NN=C3C(F)(F)F)C2

Technology Process of 4-Desfluoro N-boc sitagliptin

There total 11 articles about 4-Desfluoro N-boc sitagliptin 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: 92.0%

3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (486460-21-3) + (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid (486459-98-7) → 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)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/jm0493156

Reference yield:

3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine (486460-20-2) → 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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In 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-[(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)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jm0493156

upstream raw materials:

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

di-tert-butyl dicarbonate

2-(bromomethyl)-1,4-difluorobenzene

Downstream raw materials:

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