Emricasan

Base Information

• Chemical Name: Emricasan
• CAS No.: 254750-02-2
• Deprecated CAS: 624747-15-5
• Molecular Formula: C26H27F4NO7
• Molecular Weight: 569.51
• UNII: P0GMS9N47Q
• ChEMBL ID: CHEMBL197672
• DSSTox Substance ID: DTXSID10180160
• Metabolomics Workbench ID: 149460
• NCI Thesaurus Code: C76660
• Nikkaji Number: J3.566.323A
• Pharos Ligand ID: DMAJHCAFS3VU
• Wikidata: Q27077178
• Wikipedia: Emricasan
• Mol file: 254750-02-2.mol

Synonyms:3-(2-(2-tert-butylphenylaminooxalyl)aminopropionylamino)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic acid;emricasan;IDN 6556;IDN-6556;IDN6556;PF 03491390;PF-03491390;PF03491390

Chemical Property of Emricasan

Chemical Property:

• Refractive Index: 1.55
• PKA: 3.91±0.19(Predicted)
• PSA: 150.90000
• Density: 1.386 g/cm³
• LogP: 3.44610
• Storage Temp.: -20°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 569.17851286
• Heavy Atom Count: 40
• Complexity: 934

Purity/Quality:

99.0% ^*data from raw suppliers

Emricasan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)NC(CC(=O)O)C(=O)COC1=C(C(=CC(=C1F)F)F)F)NC(=O)C(=O)NC2=CC=CC=C2C(C)(C)C
• Isomeric SMILES: C[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)COC1=C(C(=CC(=C1F)F)F)F)NC(=O)C(=O)NC2=CC=CC=C2C(C)(C)C
• Recent ClinicalTrials: Companion Protocol for Methacetin Breath Test (MBT) in Conatus Protocol IDN-6556-14
• Recent EU Clinical Trials: A Multicenter, Randomized, Double-Blind, Placebo-Controlled Trial of Emricasan, an Oral Caspase Inhibitor, in Subjects with Non-alcoholic Steatohepatitis (NASH) Cirrhosis and Severe Portal Hypertension
• Uses: Emricasan is an irreversible pan-caspase inhibitor that hinders caspase-mediated apoptosis and inflammation.?In addition, Emricasan may reduce hepatic injury and liver fibrosis.

Technology Process of Emricasan

There total 18 articles about Emricasan 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%

→ Emricasan (254750-02-2,624747-15-5)

Guidance literature:

In water; isopropyl alcohol; at -5 - 50 ℃; for 46.5h; Purification / work up; PF-3,491,390 Form II;

Reference yield: 86.0%

(3S)-3-[N-(N′-(2-tert-butylphenyl)oxamyl)alaninyl]amino-5-(2′,3′,5′,6′-tetrafluorophenoxy)-4-oxopentanoic acid tert-butyl ester (254750-83-9) → Emricasan (254750-02-2,624747-15-5)

Guidance literature:

With trifluoroacetic acid; at 65 ℃; for 2h; Temperature;

Reference yield:

(3S)-3-[N-(N'-(2-tert-butylphenyl)oxamyl)alaninyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic acid benzyl ester (409369-36-4) → Emricasan (254750-02-2,624747-15-5)

Guidance literature:

(3S)-3-[N-(N'-(2-tert-butylphenyl)oxamyl)alaninyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic acid benzyl ester; With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; at 20 ℃; for 4h; under 1034.32 Torr;

In tetrahydrofuran; n-heptane; at -5 - 20 ℃; for 23h; Product distribution / selectivity; (3S)-3-[N-(N'-(2-tert-butylphenyl)oxamyl)alaninyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic acid form II;

upstream raw materials:

(3S)-3-[N-(N′-(2-tert-butylphenyl)oxamyl)alaninyl]amino-5-(2′,3′,5′,6′-tetrafluorophenoxy)-4-oxopentanoic acid tert-butyl ester

(3S)-3-[(N-benzyloxycarbonyl)-L-alaninyl]amino-5-bromo-4-oxopentanoic acid tert-butyl ester

(3S)-3-(alaninyl)amino-5-(2′,3′,5′,6′-tetrafluorophenoxy)-4-hydroxypentanoic acid tert-butyl ester

(3S)-3-[(N-benzyloxycarbonyl)alaninyl]amino-5-(2′,3′,5′,6′-tetrafluorophenoxy)-4-hydroxypentanoic acid tert-butyl ester

Refernces

• 1、 -. "METHODS OF USING CASPASE INHIBITORS IN TREATMENT OF LIVER DISEASE". Paragraph 00165. . Retrieved 2017/07/14.
• 2、 -. "CRYSTALLINE FORMS OF ( 3 S ) -3- [N- (N' - (2-TERT-BUTYLPHENYL) OXAMYL) ALANIWYL] AMINO-5- (2 ', 3 ', 5 ', 6 ' -TETRAFLUORO PHENOXY) -4-0X0PENTA NOIC ACID". Page/Page column 9-10. . Retrieved 2008/12/06.