N-[1,1'-Biphenyl]-2-yl-1-[2-[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl-2-pyrrolidinedicarboxamide

Base Information

• Chemical Name: N-[1,1'-Biphenyl]-2-yl-1-[2-[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl-2-pyrrolidinedicarboxamide
• CAS No.: 916141-36-1
• Molecular Formula: C₂₇H₂₆N₄O₂S
• Molecular Weight: 470.595
• Mol file: 916141-36-1.mol

Synonyms:CS-916;TCS-102;TCS 1102;TCS1102; TCS-1102;TCS 1102 , CID11960895;N-2-Biphenylyl-1-{[(1-methyl-1H-benzimidazol-2-yl)sulfanyl]acetyl }-L-prolinamide;(2S)-1-[2-(1-METHYLBENZIMIDAZOL-2-YL)SULFANYLACETYL]-N-(2-PHENYLPHENYL)PYRROLIDINE-2-CARBOXAMIDE;N-[1,1'-Biphenyl]-2-yl-1-[2-[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl-2-pyrrolidinedicarboxamide;(2S)-N-[1,1'-Biphenyl]-2-yl-1-[2-[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl]-2-pyrrolidinecarboxamide;(2S)- 2-Pyrrolidinecarboxamide, N-[1,1'-biphenyl]-2-yl-1-[2-[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl]

Chemical Property of N-[1,1'-Biphenyl]-2-yl-1-[2-[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl-2-pyrrolidinedicarboxamide

Chemical Property:

• PSA: 96.02000
• LogP: 5.54950
• Storage Temp.: Store at RT

Purity/Quality:

99%+, ^*data from raw suppliers

TCS1102 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Orexin receptors 1 (OX1R) and OX2R mediate the action of the neuropeptides orexin A and orexin B. TCS 1102 is a dual antagonist of both OX1R and OX2R (Kis = 0.2 and 3 nM, respectively). It is a poor substrate for P-glycoprotein and, as a result, demonstrates good brain penetration when administered intraperitoneally. Dual orexin receptor antagonists, including TCS 1102, promote sleep and prevent drug-induced plasticity and drug relapse. Systemic injection of TCS 1102 (10 mg/kg i.p.) in rats decreases fear and anxiety in response to acute episodes of stress.
• Uses: TCS 1102 is a dual antagonist of both OX1R and OX2R. It is a poor substrate for P-glycoprotein and, as a result, demonstrates good brain penetration when administered intraperitoneally. Dual orexin receptor antagonists, including TCS 1102, promote sleep and prevent drug-induced plasticity and drug relapse.

Technology Process of N-[1,1'-Biphenyl]-2-yl-1-[2-[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl-2-pyrrolidinedicarboxamide

There total 9 articles about N-[1,1'-Biphenyl]-2-yl-1-[2-[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl-2-pyrrolidinedicarboxamide 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: 32.0%

(S)-1-(2-((1H-benzo[d]imidazol-2-yl)thio) acetyl)-N-([1,1'-biphenyl]-2-yl)pyrrolidine-2-carboxamide + methyl iodide (74-88-4) → N-biphenyl-2-yl-1-[[(1-methyl-1H-benzimidazol-2-yl)-sulfanyl]acetyl]-L-prolinamide (916141-36-1)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2012.01.114

Reference yield:

C15H17N3O3S (916143-36-7) + 2-phenylaniline (90-41-5) → N-biphenyl-2-yl-1-[[(1-methyl-1H-benzimidazol-2-yl)-sulfanyl]acetyl]-L-prolinamide (916141-36-1)

Guidance literature:

With pyridine; trichlorophosphate; at 0 ℃; for 0.333333h;

Reference yield:

(S)-2-([1,1'-biphenyl]-2-yl)-1-(1-(2-bromo-acetyl)pyrrolidin-2-yl)ethanone + 1-methyl-1H-benzimidazole-2-thiol (2360-22-7) → N-biphenyl-2-yl-1-[[(1-methyl-1H-benzimidazol-2-yl)-sulfanyl]acetyl]-L-prolinamide (916141-36-1)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 60 ℃; microwave irradiation;

DOI:10.1016/j.bmcl.2008.01.001

upstream raw materials:

C₁₅H₁₇N₃O₃S

2-phenylaniline

1-methyl-1H-benzimidazole-2-thiol

Benzimidazol-2-thiol

Refernces

• 1、 Bergman, Jeffrey M.,Roecker, Anthony J.,Mercer, Swati P.,Bednar, Rodney A.,Reiss, Duane R.,Ransom, Richard W.,Meacham Harrell,Pettibone, Douglas J.,Lemaire, Wei,Murphy, Kathy L.,Li, Chunze,Prueksaritanont, Thomayant,Winrow, Christopher J.,Renger, John J.,Koblan, Kenneth S.,Hartman, George D.,Coleman, Paul J.. "Proline bis-amides as potent dual orexin receptor antagonists". . p. 1425 - 1430. Retrieved 2008/12/21.