Pentanamide, N-(cyanomethyl)-4-methyl-2-(((1S)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)(1,1'-biphenyl)-4-yl)ethyl)amino)-, (2S)-

Base Information

• Chemical Name: Pentanamide, N-(cyanomethyl)-4-methyl-2-(((1S)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)(1,1'-biphenyl)-4-yl)ethyl)amino)-, (2S)-
• CAS No.: 603139-12-4
• UNII: 29250PP3ON
• Nikkaji Number: J2.747.365B
• Wikidata: Q27078443
• Pharos Ligand ID: Y5UB7UZ87JY1
• ChEMBL ID: CHEMBL437501
• Mol file: 603139-12-4.mol

Synonyms:L-873724

Chemical Property of Pentanamide, N-(cyanomethyl)-4-methyl-2-(((1S)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)(1,1'-biphenyl)-4-yl)ethyl)amino)-, (2S)-

Chemical Property:

• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 481.16469736
• Heavy Atom Count: 33
• Complexity: 785

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)NCC#N)NC(C1=CC=C(C=C1)C2=CC=C(C=C2)S(=O)(=O)C)C(F)(F)F
• Isomeric SMILES: CC(C)C[C@@H](C(=O)NCC#N)N[C@@H](C1=CC=C(C=C1)C2=CC=C(C=C2)S(=O)(=O)C)C(F)(F)F

Technology Process of Pentanamide, N-(cyanomethyl)-4-methyl-2-(((1S)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)(1,1'-biphenyl)-4-yl)ethyl)amino)-, (2S)-

There total 13 articles about Pentanamide, N-(cyanomethyl)-4-methyl-2-(((1S)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)(1,1'-biphenyl)-4-yl)ethyl)amino)-, (2S)- 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: 79.0%

(S)-4-methyl-2-(((S)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethyl)amino)pentanoic acid (603142-83-2) + 2-aminoacetonitrile hydrochloride (6011-14-9) → (2S)-4-methyl-2-[(1S)-2,2,2-trifluoro-1-(4'-methanesulfonyl-biphenyl-4-yl)ethylamino]-pentanoic acid cyanomethyl-amide (603139-12-4)

Guidance literature:

With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1021/jo052430j

Reference yield:

(S)-3-methyl-1-triethylsilanyloxymethyl-butylamine (896743-06-9) → (2S)-4-methyl-2-[(1S)-2,2,2-trifluoro-1-(4'-methanesulfonyl-biphenyl-4-yl)ethylamino]-pentanoic acid cyanomethyl-amide (603139-12-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 80 percent / DMAP*HCl / toluene / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -74 °C

2.2: 91 percent / tetrahydrofuran; hexane / 1 h / -75 °C

3.1: 88 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 1 h / 10 - 25 °C

4.1: 78 percent / Na₂CO₃; PPh₃ / Pd(OAc)2 / propan-1-ol; H₂O / 2.5 h / 89 °C

5.1: 94 percent / Bu₄NHSO₄; Na₂WO₄*2H₂O; H₂O₂ / toluene; H₂O / 4 h / 23 - 30.8 °C

6.1: H₅IO₆; CrO₃ / acetonitrile; H₂O / 0 - 5 °C

7.1: 79 percent / HATU; Et₃N / dimethylformamide / 1 h / 0 °C

With chromium(VI) oxide; sodium tungstate; n-butyllithium; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; 4-(dimethylamino)pyridine hydrochloride; sodium carbonate; periodic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium diacetate; In tetrahydrofuran; propan-1-ol; hexane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: Suzuki cross-coupling;

DOI:10.1021/jo052430j

Reference yield:

((S)-3-methyl-1-triethylsilanyloxymethyl-butyl)-[2,2,2-trifluoro-eth-(E)-ylidene]amine (896743-07-0) → (2S)-4-methyl-2-[(1S)-2,2,2-trifluoro-1-(4'-methanesulfonyl-biphenyl-4-yl)ethylamino]-pentanoic acid cyanomethyl-amide (603139-12-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -74 °C

1.2: 91 percent / tetrahydrofuran; hexane / 1 h / -75 °C

2.1: 88 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 1 h / 10 - 25 °C

3.1: 78 percent / Na₂CO₃; PPh₃ / Pd(OAc)2 / propan-1-ol; H₂O / 2.5 h / 89 °C

4.1: 94 percent / Bu₄NHSO₄; Na₂WO₄*2H₂O; H₂O₂ / toluene; H₂O / 4 h / 23 - 30.8 °C

5.1: H₅IO₆; CrO₃ / acetonitrile; H₂O / 0 - 5 °C

6.1: 79 percent / HATU; Et₃N / dimethylformamide / 1 h / 0 °C

With chromium(VI) oxide; sodium tungstate; n-butyllithium; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; periodic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium diacetate; In tetrahydrofuran; propan-1-ol; hexane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Suzuki cross-coupling;

DOI:10.1021/jo052430j

upstream raw materials:

(S)-4-methyl-2-(((S)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethyl)amino)pentanoic acid

2-aminoacetonitrile hydrochloride

N-{(1S)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)biphenyl-4-yl]ethyl}-L-leucylglycinamide

2-aminoacetonitrile

Refernces

• 1、 Leger, Serge,Bayly, Christopher I.,Black, W. Cameron,Desmarais, Sylvie,Falgueyret, Jean-Pierre,Masse, Frederic,Percival, M. David,Truchon, Jean-Francois. "Primary amides as selective inhibitors of cathepsin K". . p. 4328 - 4332. Retrieved 2008/02/10.
• 2、 Roy, Amelie,Gosselin, Francis,O'Shea, Paul D.,Chen, Cheng-Y. "Diastereoselective arylithium addition to an α-trifluoromethyl imine. Practical synthesis of a potent cathepsin K inhibitor". . p. 4320 - 4323. Retrieved 2007/10/03.