ARN-509

Base Information

• Chemical Name: ARN-509
• CAS No.: 956104-40-8
• Molecular Formula: C21H15F4N5O2S
• Molecular Weight: 477.442
• Mol file: 956104-40-8.mol

Synonyms:ARN-509; Apalutamide

Chemical Property of ARN-509

Chemical Property:

• PKA: 13.83±0.46(Predicted)
• PSA: 121.42000
• Density: 1.59±0.1 g/cm3(Predicted)
• LogP: 4.05248
• Solubility.: ≥23.85 mg/mL in DMSO; insoluble in H2O; ≥7.33 mg/mL in EtOH

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

Apalutamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: ARN-509 is a selective and competitive androgen receptor inhibitor with IC50 of 16 nM in a cell-free assay, useful for prostate cancer treatment. Phase 3.
• Uses: Apalutamide is a second-generation antiandrogen used in the treatment of prostate cancer. It is a potent antagonist of androgen receptor with IC50 value of 16 nM. Binds androgen receptors, thereby inhibiting nuclear translocation, DNA binding and transcriptional activation. ARN-509 has therapeutic applications in non-metastatic, castration-resistant prostate cancer.

Technology Process of ARN-509

There total 61 articles about ARN-509 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: 90.0%

4-(1-cyano-cyclobutanylamino)-2-fluoro-N-methyl-benzamide (915087-26-2) + 5-isothiocyanato-3-(trifluoromethyl)pyridine-2-carbonitrile (951753-87-0) → ARN-509 (956104-40-8)

Guidance literature:

4-(1-cyano-cyclobutanylamino)-2-fluoro-N-methyl-benzamide; 5-isothiocyanato-3-(trifluoromethyl)pyridine-2-carbonitrile; With triethylsilyl chloride; In N,N-dimethyl acetamide; toluene; at 25 - 65 ℃; for 23h;

With hydrogenchloride; In N,N-dimethyl acetamide; toluene; at 53 - 58 ℃; for 6h;

Reference yield: 90.0%

methyl 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-fluorobenzoate + methylamine (74-89-5) → ARN-509 (956104-40-8)

Guidance literature:

In water; at 20 - 30 ℃; for 1h;

Reference yield: 90.0%

5-isothiocyanato-3-(trifluoromethyl)pyridine-2-carbonitrile (951753-87-0) + S-phenyl 1-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)cyclobutane-1-thiocarboxylate → ARN-509 (956104-40-8)

Guidance literature:

In Isopropyl acetate; dimethyl sulfoxide; at 90 ℃; for 24h; Inert atmosphere;

upstream raw materials:

5-amino-3-(trifluoromethyl)pyridine-2-carbonitrile

4-(1-cyano-cyclobutanylamino)-2-fluoro-N-methyl-benzamide

thiophosgene

2-cyano-3-(trifluoromethyl)-5-nitropyridine

Refernces

• 1、 -. "Method for preparing". Paragraph 0100-0104. . Retrieved 2021/08/25.
• 2、 -. "PROCESS FOR THE PREPARATION OF APALUTAMIDE". Paragraph 11-12. . Retrieved 2021/02/26.