441741-66-8

Basic information

• Product Name: Panobinostat Carboxylic Acid Methyl Ester Hydrochloride
• Synonyms: Panobinostat Carboxylic Acid Methyl Ester Hydrochloride;(2E)-3-[4-[[[2-(2-Methyl-1H-indol-3-yl)ethyl]aMino]Methyl]phenyl]-2-propenoic Acid Methyl Ester, Hydrochloride
• CAS NO: 441741-66-8
• Molecular Formula: C₂₂H₂₄N₂O₂*ClH
• Molecular Weight: 383.89116
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 441741-66-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane,
• CAS DataBase Reference: Panobinostat Carboxylic Acid Methyl Ester Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Panobinostat Carboxylic Acid Methyl Ester Hydrochloride(441741-66-8)
• EPA Substance Registry System: Panobinostat Carboxylic Acid Methyl Ester Hydrochloride(441741-66-8)

Safety Data

• Hazardous Substances Data: 441741-66-8(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

Intermediate in the preparation of Panobinostat

Upstream product

• 441741-65-7 (E)-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]acrylic acid methyl ester 
• 2731-06-8 2-methyltryptamine 
• 7560-50-1 methyl (2E)-3-(4-formylphenyl)acrylate 
• 1067-74-9 Methyl diethylphosphonoacetate 
• 73291-09-5 4-chloromethylbenzaldehyde 

Downstream Products

• 404950-80-7 panobinostat 

Relevant articles and documents

An improved and efficient synthesis of panobinostat

An improved and efficient method for the synthesis of panobinostat was developed. The commercially available starting material 4-(chloromethyl)benzaldehyde was converted to (E)-methyl 3-[4-(chloromethyl)phenyl]acrylate via the Wittig-Horner reaction and was then directly condensed with 2-(2-methyl-1H-indol-3-yl)ethanamine to afford the key intermediate (E)-methyl 3-[4-({[2-(2-methyl-1H-indol- 3-yl)ethyl]amino}methyl)phenyl]acrylate in a one-pot synthesis reactor. Subsequently a nucleophilic substitution reaction was carried out smoothly to generate the desired compound. The key intermediate and target compound were characterised by HRMS, 1H NMR and 13C NMR. This procedure is operationally simple and would be more suitable for industrial production.

Synthesis method of panobinostat

The invention discloses a synthesis method of panobinostat. The synthesis method comprises a step of synthesizing 2-methyl tryptamine or hydrochloride thereof, namely taking 2-methylindole as a raw material, conducting reaction with chloroacetyl chloride or bromoacetyl bromide, and conducting reaction with potassium phthalimide to obtain the 2-methyl tryptamine. According to the technical scheme adopted by the invention, influence of toxic raw materials on the safety of a panobinostat product is avoided; meanwhile, the invention provides the synthesis method applicable to industrial production.

METHOD OF USE OF DEACETYLASE INHIBITORS

The present invention provides methods of treating and/or preventing pathologic cardiac hypertrophy and heart failure comprising administering hydroxamate compounds which are deacetylase inhibitors.