methyl (2S)-2-[[4-[(1H-imidazol-5-ylmethylamino)methyl]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoate

Base Information

• Chemical Name: methyl (2S)-2-[[4-[(1H-imidazol-5-ylmethylamino)methyl]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoate
• CAS No.: 344900-92-1
• Molecular Formula: C25H30N4O3S
• Molecular Weight: 466.59600
• UNII: SA7S7H5D4B
• Nikkaji Number: J1.244.740J
• ChEMBL ID: CHEMBL138719
• Mol file: 344900-92-1.mol

Synonyms:FTI-2153;344900-92-1;SA7S7H5D4B;CHEMBL138719;FTI2153;methyl (2S)-2-[[4-[(1H-imidazol-5-ylmethylamino)methyl]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoate;(S)-Methyl 2-(5-((((1H-imidazol-5-yl)methyl)amino)methyl)-2'-methyl-(1,1'-biphenyl)-2-ylcarboxamido)-4-(methylthio)butanoate;L-Methionine, N-((5-(((1H-imidazol-4-ylmethyl)amino)methyl)-2'-methyl(1,1'-biphenyl)-2-yl)carbonyl)-, methyl ester;L-Methionine, N-((5-(((1H-imidazol-5-ylmethyl)amino)methyl)-2'-methyl(1,1'-biphenyl)-2-yl)carbonyl)-, methyl ester;L-Methionine,N-[[5-[[(1H-imidazol-4-ylmethyl)amino]methyl]-2'-methyl[1,1'-biphenyl]-2-yl]carbonyl]-, methyl ester;UNII-SA7S7H5D4B;SCHEMBL6776331;EX-A4723;BDBM50097814;AKOS040741771;MS-28606;HY-123242;CS-0082232;(S)-2-[(5-{[(1H-Imidazol-4-ylmethyl)-amino]-methyl}-2''-methyl-biphenyl-2-carbonyl)-amino]-4-methylsulfanyl-butyric acid methyl ester

Chemical Property of methyl (2S)-2-[[4-[(1H-imidazol-5-ylmethylamino)methyl]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoate

Chemical Property:

• Boiling Point: 700.1±60.0 °C(Predicted)
• PSA: 121.41000
• Density: 1.210±0.06 g/cm3(Predicted)
• LogP: 4.48120
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 466.20386201
• Heavy Atom Count: 33
• Complexity: 623

Purity/Quality:

99%+, ^*data from raw suppliers

FTI-2153 98.41% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C2=C(C=CC(=C2)CNCC3=CN=CN3)C(=O)NC(CCSC)C(=O)OC
• Isomeric SMILES: CC1=CC=CC=C1C2=C(C=CC(=C2)CNCC3=CN=CN3)C(=O)N[C@@H](CCSC)C(=O)OC

Technology Process of methyl (2S)-2-[[4-[(1H-imidazol-5-ylmethylamino)methyl]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoate

There total 11 articles about methyl (2S)-2-[[4-[(1H-imidazol-5-ylmethylamino)methyl]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoate 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: 54.0%

2-[(5-aminomethyl-2'-methylbiphenyl-2-carbonyl)amino]-4-methylsulfanylbutyric acid methyl ester (722454-00-4) + 4(5)formylimidazole (3034-50-2) → FTI-2153 (344900-92-1)

Guidance literature:

2-[(5-aminomethyl-2'-methylbiphenyl-2-carbonyl)amino]-4-methylsulfanylbutyric acid methyl ester; 4⁽⁵⁾formylimidazole; In methanol; at 20 ℃; for 0.5h;

With sodium tetrahydroborate; In methanol; for 36h;

DOI:10.1016/j.bmc.2004.09.020

Reference yield:

5-cyano-2'-methyl-biphenyl-2-carboxylic acid methyl ester (478908-75-7) → FTI-2153 (344900-92-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 92 percent / hydrogen / palladium on carbon / tetrahydrofuran / 3102.89 Torr

2.1: 99 percent / lithium hydroxide / tetrahydrofuran; H₂O; methanol / Heating

3.1: 69 percent / HOBt; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; triethylamine / CH₂Cl₂ / 36 h / 20 °C

4.1: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

5.1: methanol / 0.5 h / 20 °C

5.2: 54 percent / sodium borohydride / methanol / 36 h

With lithium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.bmc.2004.09.020

Reference yield:

2-bromo-4-nitrobenzoic acid (16426-64-5) → FTI-2153 (344900-92-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 82 percent / thionyl chloride / Heating

2.1: tetrakis(triphenylphosphine)palladium⁽⁰⁾ / dimethylformamide / 0.17 h

2.2: 92 percent / potassium carbonate / dimethylformamide / 80 - 120 °C

3.1: 93 percent / tin(II) chloride dihydrate / ethyl acetate / 4 h / Heating

4.1: sodium nitrite; hydrochloric acid; acetic acid / H₂O; methanol / 0 °C

4.2: 83 percent / potassium iodide; hydrochloric acid / H₂O; methanol / 0.25 h / 60 °C

5.1: 68 percent / N-methyl-2-pyrrolidinone / 4 h / 200 °C

6.1: 92 percent / hydrogen / palladium on carbon / tetrahydrofuran / 3102.89 Torr

7.1: 99 percent / lithium hydroxide / tetrahydrofuran; H₂O; methanol / Heating

8.1: 69 percent / HOBt; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; triethylamine / CH₂Cl₂ / 36 h / 20 °C

9.1: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

10.1: methanol / 0.5 h / 20 °C

10.2: 54 percent / sodium borohydride / methanol / 36 h

With 1-methyl-pyrrolidin-2-one; hydrogenchloride; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; tin(ll) chloride; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 2.2: Suzuki coupling / 4.2: Sandmeyer reaction;

DOI:10.1016/j.bmc.2004.09.020

upstream raw materials:

2-[(5-aminomethyl-2'-methylbiphenyl-2-carbonyl)amino]-4-methylsulfanylbutyric acid methyl ester

4⁽⁵⁾formylimidazole

5-cyano-2'-methyl-biphenyl-2-carboxylic acid methyl ester

5-(tert-butoxycarbonylamino-methyl)-2'-methyl-biphenyl-2-carboxylic acid methyl ester

Refernces