234082-05-4

Basic information

• Product Name: ethyl 4-((3S,5R)-3,5-diMethylpiperazin-1-yl)benzoate
• Synonyms: ethyl 4-((3S,5R)-3,5-diMethylpiperazin-1-yl)benzoate;Ethyl4-[(3R,5S)-3,5-dimethylpiperazin-1-yl]benzoate
• CAS NO: 234082-05-4
• Molecular Formula: C₁₅H₂₂N₂O₂
• Molecular Weight: 262.35
• Mol File: 234082-05-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 4-((3S,5R)-3,5-diMethylpiperazin-1-yl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-((3S,5R)-3,5-diMethylpiperazin-1-yl)benzoate(234082-05-4)
• EPA Substance Registry System: ethyl 4-((3S,5R)-3,5-diMethylpiperazin-1-yl)benzoate(234082-05-4)

Safety Data

• Hazardous Substances Data: 234082-05-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 4-((3S,5R)-3,5-dimethylpiperazin-1-yl)benzoate is used as an intermediate in the manufacturing of pharmaceuticals for its unique molecular structure and potential therapeutic benefits.
Used in Central Nervous System Drug Synthesis:
Ethyl 4-((3S,5R)-3,5-dimethylpiperazin-1-yl)benzoate is used as a building block in the synthesis of drugs that act on the central nervous system, due to its potential to contribute to the development of new medications.
Used in Neurological and Psychiatric Disorder Treatment:
Ethyl 4-((3S,5R)-3,5-dimethylpiperazin-1-yl)benzoate is used as a potential candidate for the treatment of various neurological and psychiatric disorders, owing to its piperazine moiety.

Upstream product

• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 21655-48-1 cis-2,6-dimethylpiperazine 

Downstream Products

• 234082-06-5 ethyl 4-{cis-3,5-dimethyl-4-(pyrimidin-2-yl)piperazin-1-yl}benzoate 
• 234082-07-6 4-{cis-3,5-dimethyl-4-(pyrimidin-2-yl)piperazin-1-yl}benzoic acid 
• 1035271-21-6 4-((3R,5S)-3,4,5-trimethylpiperazin-1-yl)benzoate 
• 1035269-85-2 N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]-4-[(3R,5S)-3,5-dimethylpiperazin-1-yl]benzamide 

Relevant articles and documents

New and convergent synthesis of AZD 4547

A practical and convergent synthetic route of AZD 4547 was developed successfully. The intermediate 5-(3,5-dimethoxyphenylethyl)-1H-pyrazol-3-amine (7) was prepared from 3,5-dimethoxybenzaldehyde through 6 simple steps in 52.3% yield. Another intermediate 4-((3S,5R)-3,5-dimethylpiperazin-1-yl)benzoic acid (14) was synthesized from ethyl 4-fluorobenzoate and (2R,6S)-2,6-dimethylpiperazine in 62% yield over 2 steps. Finally, AZD 4547 was obtained from 7 and 14 in 73% yield and 99.1% purity. Purification methods of the intermediates and the final product involved in the route were developed.

Method for preparing AZD4547, intermediate and preparation method of intermediate

The invention provides a method for preparing AZD-4547. The method comprises the following steps: (1) preparing a first intermediate 2-cyano-5-(3, 5-dimethoxyphenyl)-3-oxoethyl valerate; (2) preparinga second intermediate 5-[2-(3, 5-dimethoxyphenyl) ethyl]-1H-pyrazole-3-amine by taking the first intermediate as a raw material; and (3) in an alkali-containing organic solvent, carrying out a reaction on a third intermediate 4-((3S, 5R)-3, 5-dimethylpiperazinyl-1-yl) benzoyl chloride and the second intermediate to prepare the AZD-4547. The method has the advantages of accessible raw materials, simple technique, mild reaction conditions, convenient operation, high yield and low cost and can easily implement industrial production. The invention also provides an intermediate 2-cyano-5-(3, 5-dimethoxyphenyl)-3-oxoethyl valerate for preparing AZD-4547 and a preparation method thereof.

Design, synthesis and biological evaluation of a series of novel 2-benzamide-4-(6-oxy-N-methyl-1-naphthamide)-pyridine derivatives as potent fibroblast growth factor receptor (FGFR) inhibitors

Starting from the phase II clinical FGFR inhibitor lucitanib (2), we conducted a medicinal chemistry approach by opening the central quinoline skeleton coupled with a scaffold hopping process thus leading to a series of novel 2-benzamide-4-(6-oxy-N-methyl-1-naphthamide)-pyridine derivatives. Compound 25a was identified to show selective and equally high potency against FGFR1/2 and VEGFR2 with IC50 values less than 5.0 nM. Significant antiproliferative effects on both FGFR1/2 and VEGFR2 aberrant cancer cells were observed. In the SNU-16 xenograft model, compound 25a showed tumor growth inhibition rates of 25.0% and 81.0% at doses of 10 mg/kg and 50 mg/kg, respectively, with 5% and 10%body weight loss. In view of the synergistic potential of FGFs and VEGFs in tumor angiogenesis observed in preclinical studies, the FGFR/VEGFR2 dual inhibitor 25a may achieve better clinical benefits.

Development of an SNAr Reaction: A Practical and Scalable Strategy to Sequester and Remove HF

A simple and operationally practical method to sequester and remove fluoride generated through the SNAr reaction between amines and aryl fluorides is reported. Calcium propionate acts as an inexpensive and environmentally benign in situ scrubbe

Development of an SNAr Reaction: A Practical and Scalable Strategy to Sequester and Remove HF

A simple and operationally practical method to sequester and remove fluoride generated through the SNAr reaction between amines and aryl fluorides is reported. Calcium propionate acts as an inexpensive and environmentally benign in situ scrubbe

Pyrazolo [3,4 - the b] pyridine and [...] composition preparation method and use of (by machine translation)

The present invention provides a pyrazolo [3,4 - the b] pyridine and [...] compound of preparation and use, in particular, the present invention provides a following formula (I) compounds are shown, wherein the definition of each group as described in the specification. The compounds of the invention has excellent tyrosine kinase inhibiting activity, so can be used for preparing a series of treating diseases associated with the tyrosine kinase activity of the drug. (by machine translation)

NOVEL COMPOUNDS

There is provided a compound of formula (I): or a pharmaceutically acceptable salt thereof. There are also provided processes for the manufacture of a compound of Formula 1, and the use of a compound of Formula 1 as a medicament and in the treatment of cancer.

Tricyclic pharmacophore-based molecules as novel integrin αvβ3 antagonists. Part 1: Design and synthesis of a lead compound exhibiting αvβ3/ αIIbβ3 dual antagonistic activity

In order to generate novel compounds with integrin α vβ3-antagonistic activity together with antiplatelet activity, tricyclic pharmacophore-based molecules were designed and synthesized. Although piperazine-containing compounds initially prepared were selective αIIbβ3 antagonists, replacement of piperazine with piperidine furnished a potent αvβ3/ αIIbβ3 dual antagonist. Structure-activity relationship (SAR) studies provided clues for further development of tricyclic pharmacophore-based integrin antagonists.

Phenylpiperazine derivatives as integrin αvβ3 antagonists

An objective of the present invention is to provide compounds having integrin αvβ3 antagonistic activity, GP IIb/IIIa antagonistic activity, and/or human platelet aggregation inhibitory activity, and therapeutic agents for treating integrin αvβ3-mediated diseases and for inhibiting platelet aggregation. The derivatives according to the present invention are compounds represented by formula (I) or pharmaceutically acceptable salts or solvates thereof: wherein A represents a five- to seven-membered heterocyclic ring containing two nitrogen atoms or the like; X and Z represent CH or a nitrogen atom; R4 and R5 represent alkyl, halogen or the like; Q represents >C=O, >CH2 or the like; R6 represents H, alkyl, aralkyl or the like; R7 represents H, alkynyl or the like; R8 represents H, substituted amino or the like; R9 represents H or alkyl; m is 0 to 5; n is 0 to 4; p is 2 or 3; and q is 0 or 1.