Piragliatin

Base Information

• Chemical Name: Piragliatin
• CAS No.: 625114-41-2
• Molecular Formula: C19H20ClN3O4S
• Molecular Weight: 421.904
• UNII: BM1HR7IP1L
• DSSTox Substance ID: DTXSID3048520
• Nikkaji Number: J3.485.118B
• Wikidata: Q27274751
• NCI Thesaurus Code: C77587
• Metabolomics Workbench ID: 144372
• ChEMBL ID: CHEMBL1783734
• Mol file: 625114-41-2.mol

Synonyms:piragliatin;RO4389620

Chemical Property of Piragliatin

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 421.0863050
• Heavy Atom Count: 28
• Complexity: 681

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)C1=C(C=C(C=C1)C(CC2CCC(=O)C2)C(=O)NC3=NC=CN=C3)Cl
• Isomeric SMILES: CS(=O)(=O)C1=C(C=C(C=C1)[C@@H](C[C@H]2CCC(=O)C2)C(=O)NC3=NC=CN=C3)Cl
• Recent EU Clinical Trials: A phase 2, multicenter, open label, titration study to assess the efficacy, safety and tolerability of RO4389620 in doses up to 200 mg BID in patients with type 2 diabetes mellitus not optimally controlled with previous treatment with one oral antihyperglycemic agent.

Technology Process of Piragliatin

There total 10 articles about Piragliatin 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: 66.0%

2-Aminopyrazine (5049-61-6) + 2(R)-(3-chloro-4-methanesulfonylphenyl)-3-((S)-3-oxo-cyclopentyl)propionic acid → Piragliatin (625114-41-2)

Guidance literature:

2(R)-(3-chloro-4-methanesulfonylphenyl)-3-((S)-3-oxo-cyclopentyl)propionic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; toluene; for 1h; Nitrogen atmosphere;

2-Aminopyrazine; With pyridine; In dichloromethane; at 25 ℃; for 18h;

Reference yield: 43.0%

2-Aminopyrazine (5049-61-6) + (2R)-2-(3-chloro-4-methanesulfonylphenyl)-3-[(1R)-3-oxocyclopentyl]propanoic acid (625114-43-4) → Piragliatin (625114-41-2)

Guidance literature:

(2R)-2-(3-chloro-4-methanesulfonylphenyl)-3-[(1R)-3-oxocyclopentyl]propanoic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; toluene; at 25 ℃; for 1h; Inert atmosphere;

2-Aminopyrazine; With pyridine; In tetrahydrofuran; dichloromethane; at -10 - 25 ℃; for 18h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jm3008689

Reference yield:

2-Aminopyrazine (5049-61-6) + (R)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-((R)-3-oxo-cyclopentyl)-propionyl chloride (1003013-93-1) → Piragliatin (625114-41-2)

Guidance literature:

With pyridine; In dichloromethane; at -16 - -5 ℃; for 1.86667h; Product distribution / selectivity;

upstream raw materials:

2-Aminopyrazine

(R)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-((R)-3-oxo-cyclopentyl)-propionyl chloride

2-chlorothioanisole

(2R)-2-(3-chloro-4-methanesulfonylphenyl)-3-[(1R)-3-oxocyclopentyl]propanoic acid

Downstream raw materials:

iso-propanol solvate of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-((R)-3-oxo-cyclopentyl)-N-pyrazin-2-yl-propionamide

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF AN ISOPROPANOL SOLVATE OF A GLUCOKINASE ACTIVATOR". Page/Page column 5; 7; 10. . Retrieved 2010/11/28.
• 2、 -. "Substituted-cycloalkyl and oxygenated-cycloalkyl glucokinase activators". Page 42. . Retrieved 2010/11/30.