4-[7-[4-cyano-3-(trifluoromethyl)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide

Base Information

• Chemical Name: 4-[7-[4-cyano-3-(trifluoromethyl)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide
• CAS No.: 915087-27-3
• Molecular Formula: C₂₂H₁₆F₄N₄O₂S
• Molecular Weight: 476.454
• UNII: 5ZE6THH5VF
• DSSTox Substance ID: DTXSID301337376
• Nikkaji Number: J2.648.986E
• Wikipedia: RD-162
• ChEMBL ID: CHEMBL1082410
• Mol file: 915087-27-3.mol

Synonyms:915087-27-3;RD162;RD 162;RD-162;4-[7-[4-cyano-3-(trifluoromethyl)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide;5ZE6THH5VF;MLS006010318;SCHEMBL547156;CHEMBL1082410;DTXSID301337376;BCP27723;PB21237;NCGC00263137-01;NCGC00263137-02;4-[7-(4-CYANO-3-TRIFLUOROMETHYL-PHENYL)-8-OXO-6-THIOXO-5,7-DIAZA-SPIRO[3.4]OCT-5-YL]-2-FLUORO-N-METHYL-BENZAMIDE;SMR004701383;HY-111145;CS-0034409;4-[7-[4-Cyano-3-(trifluoromethyl)phenyl]-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-2-fluoro-N-methylbenzamide;Benzamide, 4-[7-[4-cyano-3-(trifluoromethyl)phenyl]-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-2-fluoro-N-methyl-;N-methyl-4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diaza-spiro[3.4]oct-5-yl]-2-fluorobenzamide;N-Methyl-4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl]-2-fluorobenzamide

Chemical Property of 4-[7-[4-cyano-3-(trifluoromethyl)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide

Chemical Property:

• PSA: 112.02000
• Density: 1.55
• LogP: 4.84138
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 476.09300959
• Heavy Atom Count: 33
• Complexity: 883

Purity/Quality:

97% ^*data from raw suppliers

RD162 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(=O)C1=C(C=C(C=C1)N2C(=S)N(C(=O)C23CCC3)C4=CC(=C(C=C4)C#N)C(F)(F)F)F
• Uses: Depyridinyl Phenyl Apalutamide is a derivative of Apalutamide(A726120) which is a second-generation antiandrogen used in the treatment of prostate cancer.

Technology Process of 4-[7-[4-cyano-3-(trifluoromethyl)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide

There total 6 articles about 4-[7-[4-cyano-3-(trifluoromethyl)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide 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: 11.0%

4-(1-cyano-cyclobutanylamino)-2-fluoro-N-methyl-benzamide (915087-26-2) + 4-isothiocyanato 2-(trifluoromethyl)benzonitrile (143782-23-4) → 4-[7-(6-cyano-5-trifluoromethylpyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3,4]oct-5-yl]-2-fluoro-N-methylbenzamide (915087-27-3)

Guidance literature:

4-(1-cyano-cyclobutanylamino)-2-fluoro-N-methyl-benzamide; 4-isothiocyanato 2-(trifluoromethyl)benzonitrile; In N,N-dimethyl-formamide; at 120 ℃; for 16h;

With hydrogenchloride; water; In ethanol; N,N-dimethyl-formamide; for 1h; Reflux;

Reference yield:

2-fluoro-N-methyl-4-amino-benzamide (915087-25-1) → 4-[7-(6-cyano-5-trifluoromethylpyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3,4]oct-5-yl]-2-fluoro-N-methylbenzamide (915087-27-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / 16 h / 80 °C

2.1: N,N-dimethyl-formamide / 16 h / 120 °C

2.2: 1 h / Reflux

With acetic acid; In N,N-dimethyl-formamide;

Reference yield:

C22H17F4N5OS → 4-[7-(6-cyano-5-trifluoromethylpyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3,4]oct-5-yl]-2-fluoro-N-methylbenzamide (915087-27-3)

Guidance literature:

With hydrogenchloride; water; In methanol; N,N-dimethyl-formamide; for 3h; Heating / reflux;

upstream raw materials:

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

4-isothiocyanato 2-(trifluoromethyl)benzonitrile

2-fluoro-4-nitrobenzoic acid

2-fluoro-N-methyl-4-nitro-benzamide