Methyl 4-[(2-cyanopropan-2-yl)amino]benzoate

Base Information

• Chemical Name: Methyl 4-[(2-cyanopropan-2-yl)amino]benzoate
• CAS No.: 107553-81-1
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.255
• DSSTox Substance ID: DTXSID50545653
• Wikidata: Q82423219
• Mol file: 107553-81-1.mol

Synonyms:107553-81-1;METHYL 4-(2-CYANOPROPAN-2-YLAMINO)BENZOATE;Methyl 4-[(2-cyanopropan-2-yl)amino]benzoate;Methyl 4-[(1-cyano-1-methylethyl)amino]benzoate;SCHEMBL1716009;DTXSID50545653;UKRKHFCSBQHMHV-UHFFFAOYSA-N;4-[(cyanodimethylmethyl)-amino]-benzoic acid methyl ester

Chemical Property of Methyl 4-[(2-cyanopropan-2-yl)amino]benzoate

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 295

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C#N)NC1=CC=C(C=C1)C(=O)OC
• Uses: Methyl 4-[(1-cyano-1-methylethyl)amino]benzoate is an intermediate in the synthesis of Defluoro-MDV 3100 (D228590), an impurity of Enzalutamide (M199800), which is an androgen-receptor antagonist that blocks androgens from binding to the androgen receptor and prevents nuclear translocation and co-activator recruitment of the ligand-receptor complex. Enzalutamide has been shown to induce tumor cell apoptosis, and is used for the treatment of castration-resistant prostate cancer.

Technology Process of Methyl 4-[(2-cyanopropan-2-yl)amino]benzoate

There total 1 articles about Methyl 4-[(2-cyanopropan-2-yl)amino]benzoate 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: 93.0%

2-hydroxy-2-methylpropanenitrile (75-86-5) + 4-methoxycarbonyl aniline (619-45-4) → 4-[(cyanodimethylmethyl)amino]benzoic acid methyl ester (107553-81-1)

Guidance literature:

With calcium sulfate; at 105 - 110 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.bmcl.2021.128441

Reference yield: 93.0%

4-[(cyanodimethylmethyl)amino]benzoic acid methyl ester (107553-81-1) + 4-isothiocyanato 2-(trifluoromethyl)benzonitrile (143782-23-4) → 4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]benzoic acid methyl ester

Guidance literature:

4-[(cyanodimethylmethyl)amino]benzoic acid methyl ester; 4-isothiocyanato 2-(trifluoromethyl)benzonitrile; With lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile; at -42 ℃; for 0.283333h;

With hydrogenchloride; at 85 ℃; for 1h;

DOI:10.1016/j.bmcl.2021.128441

Reference yield: 80.0%

4-[(cyanodimethylmethyl)amino]benzoic acid methyl ester (107553-81-1) → acetone p-methoxycarbonylphenylimine (40938-45-2)

Guidance literature:

With tert-butoxide; In tert-butyl alcohol; 1) boiling, 2 h; 2) room temp., 6 h;

upstream raw materials:

2-hydroxy-2-methylpropanenitrile

4-methoxycarbonyl aniline

Downstream raw materials:

acetone p-methoxycarbonylphenylimine

Refernces

• 1、 Jung, Michael E.,Ouk, Samedy,Yoo, Dongwon,Sawyers, Charles L.,Chen, Charlie,Tran, Chris,Wongvipat, John. "Structure-activity relationship for thiohydantoin androgen receptor antagonists for castration-resistant prostate cancer (CRPC)". experimental part. p. 2779 - 2796. Retrieved 2010/09/05.