(2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide

Base Information

• Chemical Name: (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide
• CAS No.: 206193-17-1
• Molecular Formula: C12H10BrF3N2O2
• Molecular Weight: 351.123
• DSSTox Substance ID: DTXSID10440175
• Nikkaji Number: J949.142B
• Wikidata: Q82256415
• ChEMBL ID: CHEMBL127310
• Mol file: 206193-17-1.mol

Synonyms:206193-17-1;(R)-3-bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide;(2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide;SCHEMBL110581;CHEMBL127310;BDBM18698;DTXSID10440175;MFCD22200308;AB88562;F15286;A924369;(R)-N-[3-(Trifluoromethyl)-4-cyanophenyl]-3-bromo-2-hydroxy-2-methylpropanamide;R-2

Chemical Property of (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide

Chemical Property:

• PSA: 76.61000
• LogP: 3.31098
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 349.98777
• Heavy Atom Count: 20
• Complexity: 421

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CBr)(C(=O)NC1=CC(=C(C=C1)C#N)C(F)(F)F)O
• Isomeric SMILES: C[C@](CBr)(C(=O)NC1=CC(=C(C=C1)C#N)C(F)(F)F)O

Technology Process of (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide

There total 8 articles about (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide 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: 85.0%

(R)-3-bromo-2-hydroxy-2-methylpropanoic acid (81026-68-8) + 4-amino-2-trifluoromethylbenzonitrile (654-70-6) → (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide (206193-17-1)

Guidance literature:

(R)-3-bromo-2-hydroxy-2-methylpropanoic acid; With thionyl chloride; In tetrahydrofuran; for 2h; Inert atmosphere;

4-amino-2-trifluoromethylbenzonitrile; With triethylamine; In tetrahydrofuran; at 50 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.0c00943

Reference yield: 84.0%

4-amino-2-trifluoromethylbenzonitrile (654-70-6) + (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid (261904-39-6) → (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide (206193-17-1)

Guidance literature:

(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid; With thionyl chloride; In N,N-dimethyl acetamide; at -10 ℃; for 3h; Inert atmosphere;

4-amino-2-trifluoromethylbenzonitrile; In N,N-dimethyl acetamide; at -10 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jm5005122

Reference yield:

→ (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid (261904-39-6) + (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide (206193-17-1)

Guidance literature:

upstream raw materials:

4-amino-2-trifluoromethylbenzonitrile

3-bromomethyl-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

(R)-3-bromo-2-hydroxy-2-methylpropanoyl chloride

Downstream raw materials:

(2S)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(5-fluoro-1H-indol-1-yl)-2-hydroxy-2-methylpropanamide

Refernces

• 1、 -. "PYRAZOLYLPROPANAMIDE COMPOUNDS AND USES THEREOF FOR TREATMENT OF PROSTATE CANCER". Paragraph 00194; 00192. . Retrieved 2021/10/11.
• 2、 -. "Synthesis method of nicotinate". Paragraph 0026-0033; 0047-0055; 0068-0075. . Retrieved 2020/05/01.