JNJ 63533054

Base Information

• Chemical Name: JNJ 63533054
• CAS No.: 1802326-66-4
• Molecular Formula: C17H17ClN2O2
• Molecular Weight: 316.78
• Mol file: 1802326-66-4.mol

Synonyms:JNJ 63533054;3-Chloro-N-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]benzamide

Chemical Property of JNJ 63533054

Chemical Property:

• PSA: 58.20000
• LogP: 3.72900
• Storage Temp.: room temp
• Solubility.: Soluble in DMSO (up to 35 mg/ml).

Purity/Quality:

97% ^*data from raw suppliers

JNJ63533054 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: JNJ-63533054 (1802326-66-4) is a potent and selective brain-penetrant GPR139 agonist (EC50=16 nM) an orphan G-protein-coupled receptor expressed in the CNS.1?Tritium-labeled JNJ-63533054 binds to cell membranes expressing GPR139 and can be displaced by putative endogenous ligands.2?Decreases compulsive-like alcohol drinking and hyperalgesia in alcohol-dependent rodents.3?Suppresses morphine intake in a mouse self-administration model.4
• Uses: JNJ 63533054 is a potent and selective agonist of hGPR139 with an EC50 = 16 nM.

Technology Process of JNJ 63533054

There total 5 articles about JNJ 63533054 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: 83.0%

(S)-2-amino-N-(1-phenylethyl)acetamide hydrochloride (877614-96-5) + m-Chlorobenzoyl chloride (618-46-2) → (S)-3-chloro-N-(2-oxo-2-((1-phenylethyl)amino)ethyl)benzamide (1802326-66-4)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/acsmedchemlett.5b00247

Reference yield: 44.0%

(S)-3-bromo-5-chloro-N-(2-oxo-2-((1-phenylethyl)amino)ethyl)benzamide → (S)-3-chloro-N-(2-oxo-2-((1-phenylethyl)amino)ethyl)benzamide (1802326-66-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 1h;

DOI:10.1021/acsmedchemlett.5b00247

Reference yield:

(S)-1-phenyl-ethylamine (2627-86-3) → (S)-3-chloro-N-(2-oxo-2-((1-phenylethyl)amino)ethyl)benzamide (1802326-66-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere

2: hydrogenchloride / dichloromethane; 1,4-dioxane / 20 °C / Inert atmosphere

3: triethylamine / dichloromethane / 20 °C / Inert atmosphere

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane;

DOI:10.1021/acsmedchemlett.5b00247

upstream raw materials:

(S)-1-phenyl-ethylamine

[(1-phenylethylcarbamoyl)methyl]carbamic acid tert-butyl ester

(S)-2-amino-N-(1-phenylethyl)acetamide hydrochloride

m-Chlorobenzoyl chloride