184177-83-1

Basic information

• Product Name: 2-[(1S,2S)-1-ethyl-2-bezyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]- 3H-1,2,4-Triazol-3-one,
• Synonyms: 2-[(1S,2S)-1-ethyl-2-bezyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]- 3H-1,2,4-Triazol-3-one,;2-[(1S,2S)-1-Ethyl-2-(phenylmethoxy)propyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one;2-[(1S,2S)-1-Ethyl-2-bezyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]- 3H-1,2,4-triazol-3-one;2-((2S,3R)-2-(benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2H-1,2,4-triazol-3(4H)-one;Posaconazole side chain;[S-(R*,R*)]-2-[1-Ethyl-2-(phenylMethoxy)propyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one;1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one;1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)-piperazin-1-yl)phenyl)-1H-1,2,4-tr
• CAS NO: 184177-83-1
• Molecular Formula: C₃₀H₃₅N₅O₃
• Molecular Weight: 513.63
• EINECS: 1806241-263-5
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Posaconazole
• Mol File: 184177-83-1.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 685.351 °C at 760 mmHg
• Flash Point: 368.287 °C
• Appearance: Grey solid
• Density: 1.22
• Refractive Index: 1.632
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.18±0.30(Predicted)
• CAS DataBase Reference: 2-[(1S,2S)-1-ethyl-2-bezyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]- 3H-1,2,4-Triazol-3-one,(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(1S,2S)-1-ethyl-2-bezyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]- 3H-1,2,4-Triazol-3-one,(184177-83-1)
• EPA Substance Registry System: 2-[(1S,2S)-1-ethyl-2-bezyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]- 3H-1,2,4-Triazol-3-one,(184177-83-1)

Safety Data

• Hazardous Substances Data: 184177-83-1(Hazardous Substances Data)

Usage

Chemical Properties

Grey Solid

Uses

Intermediate in the preparation of Posaconazole (P689600).

InChI:InChI=1/C30H35N5O3/c1-3-29(23(2)38-21-24-7-5-4-6-8-24)35-30(37)34(22-31-35)27-11-9-25(10-12-27)32-17-19-33(20-18-32)26-13-15-28(36)16-14-26/h4-16,22-23,29,36H,3,17-21H2,1-2H3/t23-,29+/m1/s1

Upstream product

• 81445-44-5 (S)-2-(benzyloxy)propanal 
• 33106-32-0 2-(benzyloxy)propanoic acid 
• 100-44-7 benzyl chloride 
• 53346-03-5 2-benzyloxypropionic acid methyl ester 
• 77287-11-7 methyl (S)-2-(benzyloxy)propanoate 
• 74853-08-0 1-(4-aminophenyl)-4-(4-hydroxyphenyl)piperazine 
• 184177-81-9 phenyl N-(4-(4-(4-hydroxyphenyl)-1-piperazinyl)phenyl)carbamate 
• 170985-85-0 N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide 
• 586-78-7 para-nitrophenyl bromide 
• 7479-12-1 4-(4-(4-aminophenyl)piperazin-1-yl)benzenamine 
• 16264-05-4 1,4-bis(4-nitrophenyl)piperazine 
• 183871-36-5 C₁₂H₂₀N₂O*C₁₈H₁₄O₈ 
• 149-73-5 trimethyl orthoformate 
• 184177-88-6 C₁₇H₂₈N₂O₃ 

Downstream Products

• 170985-86-1 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-1H-1,2,4-triazol-5(4H)-one 
• 171228-49-2 posaconazote 

Relevant articles and documents

An Improved Scalable Preparation of the Antifungal Posaconazole

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Preparation method of posaconazole

The invention discloses a preparation method of posaconazole. The preparation method comprises the following steps: in a reaction solvent acetonitrile, carrying out a cyclization reaction on SM1 and SM2 under the action of an organic base namely triethanolamine to generate an intermediate 1; in a reaction solvent dimethyl sulfoxide, carrying out a nucleophilic substitution reaction on the intermediate 1 and SM3 under the action of sodium hydroxide to generate an intermediate 2; and in a reaction solvent hydrochloric acid, removing benzyl from the intermediate 2 to obtain a posaconazole crude product: heating and dissolving the posaconazole crude product, crystallizing, filtering, and drying under reduced pressure to obtain posaconazole. The preparation method has the advantages that the reaction conditions are easy to control, the product yield reaches 98.6%, the product separation and purification are simple and convenient, and the method is suitable for industrial production.

Synthesis, Crystal Structure, Anti-Bone Cancer Activity and Molecular Docking Investigations of the Heterocyclic Compound 1-((2S,3S)-2-(Benzyloxy)Pentan-3-yl) -4-(4-(4-(4-Hydroxyphenyl)Piperazin-1-yl) Phenyl)-1H-1,2,4-Triazol-5(4H)-One

Heterocyclic compound 1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (1) designed using 4-(4-(4-aminophenyl)piperazin-1-yl)phenol (2) and (S)-N′-(2-(benzyloxy)propylidene)formohydrazide (3) as start materials is successfully obtained via a multistep synthesis and finally characterized by IR, 1H NMR, and single crystal X-ray diffraction. In addition, the in vitro anticancer activities of newly synthesized compound 1 are evaluated against three human bone cancer cell lines U2OS, Saos-2, and GC9811. In addition, the molecular docking is used to study the potential antiviral activity of 1 by calculating the binding sites for the 1AS0 protein.