Orteronel

Base Information

• Chemical Name: Orteronel
• CAS No.: 426219-18-3
• Molecular Formula: C18H17N3O2
• Molecular Weight: 307.34600
• European Community (EC) Number: 687-683-4
• UNII: UE5K2FNS92
• DSSTox Substance ID: DTXSID001319121
• Nikkaji Number: J2.839.701A
• Wikipedia: Orteronel
• Wikidata: Q76411446
• NCI Thesaurus Code: C90582
• Pharos Ligand ID: BX733GLTC3XD
• Metabolomics Workbench ID: 153122
• ChEMBL ID: CHEMBL1921976
• Mol file: 426219-18-3.mol

Synonyms:6-((7S)-7-hydroxy-6,7-dihydro-5H-pyrrolo(1,2-c)imidazol-7-yl)-N-methyl-2-naphthamide;orteronel;TAK-700

Chemical Property of Orteronel

Chemical Property:

• PSA: 67.15000
• LogP: 2.42640
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 307.132076794
• Heavy Atom Count: 23
• Complexity: 471

Purity/Quality:

98% min ^*data from raw suppliers

TAK-700 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(=O)C1=CC2=C(C=C1)C=C(C=C2)C3(CCN4C3=CN=C4)O
• Isomeric SMILES: CNC(=O)C1=CC2=C(C=C1)C=C(C=C2)[C@]3(CCN4C3=CN=C4)O
• Recent ClinicalTrials: S1216, Phase III ADT+TAK-700 vs. ADT+Bicalutamide for Metastatic Prostate Cancer
• Recent EU Clinical Trials: Open label phase II clinical trial of Orteronel (TAK-700) in metastatic or advanced non-resectable granulosa cell ovarian tumors. The Greko II study.
• Recent NIPH Clinical Trials: None

Technology Process of Orteronel

There total 25 articles about Orteronel 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: 80.0%

6-[1,3-dihydroxy-1-(1-trityl-1H-imidazol-4-yl)propyl]-N-methyl-2-naphthamide (566200-77-9) → orteronel (426219-18-3,426219-23-0,426219-32-1)

Guidance literature:

6-[1,3-dihydroxy-1-(1-trityl-1H-imidazol-4-yl)propyl]-N-methyl-2-naphthamide; With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; dimethyl sulfoxide; at 0 - 8 ℃; for 1.5h;

With N-ethyl-N,N-diisopropylamine; In methanol; acetonitrile; at 60 - 63 ℃; for 2.33333h;

With ammonium chloride; In methanol; water; ethyl acetate; acetonitrile; at 25 ℃;

Reference yield: 79.0%

6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N,N-diisopropyl-2-naphthamide (1346155-60-9) + methylamine (74-89-5) → orteronel (426219-18-3,426219-23-0,426219-32-1)

Guidance literature:

methylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.833333h; Inert atmosphere;

6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N,N-diisopropyl-2-naphthamide; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 16h; Inert atmosphere;

With water; sodium chloride; In tetrahydrofuran; hexane; Inert atmosphere;

DOI:10.1016/j.bmc.2011.08.068

Reference yield: 62.0%

6-[(1S)-1,3-dihydroxy-1-(1-trityl-1H-imidazol-4-yl)propyl]-N-methyl-2-naphthamide (566200-79-1) → orteronel (426219-18-3,426219-23-0,426219-32-1)

Guidance literature:

6-[(1S)-1,3-dihydroxy-1-(1-trityl-1H-imidazol-4-yl)propyl]-N-methyl-2-naphthamide; With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 5 ℃; for 0.666667h;

In tetrahydrofuran; methanol; acetonitrile; at 60 - 65 ℃; for 4h;

With hydrogenchloride; sodium hydroxide; ammonium chloride; In tetrahydrofuran; methanol; water; acetonitrile; at 0 - 5 ℃; pH=8;

upstream raw materials:

5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one

6-[1,3-dihydroxy-1-(1-trityl-1H-imidazol-4-yl)propyl]-N-methyl-2-naphthamide

n-butyllithium

6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N,N-diisopropyl-2-naphthamide

Downstream raw materials:

Orteronel

6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methylnaphthalene-2-carboxamide

2C₁₀H₁₁NO₅*C₁₈H₁₇N₃O₂

Refernces

• 1、 -. "RELEASE-CONTROL COMPOSITION". Page/Page column 29-30. . Retrieved 2008/06/13.
• 2、 -. "Novel imidazole derivatives, production method thereof and use thereof". . . Retrieved 2008/06/13.