(S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylicacid (3,5-dimethyl-phenyl)-amide

Base Information

• Chemical Name: (S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylicacid (3,5-dimethyl-phenyl)-amide
• CAS No.: 1361321-96-1
• Molecular Formula: C₂₀H₂₄N₂O₄S
• Molecular Weight: 388.488
• Mol file: 1361321-96-1.mol

Synonyms:(S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylicacid (3,5-dimethyl-phenyl)-amide

Chemical Property of (S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylicacid (3,5-dimethyl-phenyl)-amide

Chemical Property:

Purity/Quality:

≥99% by HPLC ^*data from raw suppliers

ACT 462206 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: ACT-462206 is a potent and selective dual orexin receptor antagonist (DORA) that inhibits the stimulating effects of the orexin peptides at both the orexin 1 and 2 receptors. It decreases wakefulness and increases non-rapid eye movement (non-REM) and REM sleep while maintaining natural sleep architectures in some animal models while showing anxiolytic-like properties without affecting cognition and motor function in others.

Technology Process of (S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylicacid (3,5-dimethyl-phenyl)-amide

There total 11 articles about (S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylicacid (3,5-dimethyl-phenyl)-amide 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: 95.0%

(S)-N-(3,5-dimethylphenyl)pyrrolidine-2-carboxamide hydrochloride + 4-methoxy-phenyl-sulphonyl chloride (98-68-0) → (S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylicacid (3,5-dimethyl-phenyl)-amide (1361321-96-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 12h;

Reference yield: 95.0%

(S)-N-(3,5-dimethylphenyl)pyrrolidine-2-carboxamide hydrochloride + 4-methoxy-phenyl-sulphonyl chloride (98-68-0) → (S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylicacid (3,5-dimethyl-phenyl)-amide (1361321-96-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1002/cmdc.201402258

Reference yield: 83.0%

3,5-dimethylaminoaniline (108-69-0) + (S)-N-(p-methoxyphenylsulfonyl)proline (81242-27-5) → (S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylicacid (3,5-dimethyl-phenyl)-amide (1361321-96-1)

Guidance literature:

(S)-N-(p-methoxyphenylsulfonyl)proline; With 4-methyl-morpholine; In Isopropyl acetate; at 24 ℃; for 1h; Industrial scale;

With pivaloyl chloride; In Isopropyl acetate; at 23 - 24 ℃; Industrial scale;

3,5-dimethylaminoaniline; In Isopropyl acetate; at 3 - 5 ℃; for 3.5h; Industrial scale;

DOI:10.1021/op500277s

upstream raw materials:

4-methoxy-phenyl-sulphonyl chloride

(S)-N-(p-methoxyphenylsulfonyl)proline

3,5-dimethylaminoaniline

(S)-1-(4-Methoxy-benzenesulfonyl)-pyrrolidine-2-carbonyl chloride

Refernces

• 1、 Boss, Christoph,Roch-Brisbare, Catherine,Steiner, Michel A.,Treiber, Alexander,Dietrich, Hendrik,Jenck, Francois,Von Raumer, Markus,Sifferlen, Thierry,Brotschi, Christine,Heidmann, Bibia,Williams, Jodi T.,Aissaoui, Hamed,Siegrist, Romain,Gatfield, John. "Structure-activity relationship, biological, and pharmacological characterization of the proline sulfonamide ACT-462206: A potent, brain-penetrant dual orexin 1/orexin 2 receptor antagonist". . p. 2486 - 2496. Retrieved 2015/04/22.
• 2、 -. "PROLINE SULFONAMIDE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS". Paragraph 0257. . Retrieved 2013/06/27.