Posaconazole

Base Information

• Chemical Name: Posaconazole
• CAS No.: 171228-49-2
• Deprecated CAS: 177571-33-4
• Molecular Formula: C37H42F2N8O4
• Molecular Weight: 700.788
• European Community (EC) Number: 682-747-8
• UNII: 6TK1G07BHZ
• DSSTox Substance ID: DTXSID6049066
• Nikkaji Number: J760.534J
• Wikipedia: Posaconazole
• Wikidata: Q906453
• NCI Thesaurus Code: C61500
• RXCUI: 282446
• Pharos Ligand ID: R529WVVT6JA6
• Metabolomics Workbench ID: 63342
• ChEMBL ID: CHEMBL1397
• Mol file: 171228-49-2.mol

Synonyms:4-(p-(4-(p-(((3R,5R)-5-(2,4-difluorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-ylmethyl)-3-furyl)methoxy)phenyl)-1-piperazinyl)phenyl)-1-((1S,2S)-1-ethyl-2-hydroxypropyl)-delta(sup 2)-1,2,4-triazolin-5-one;Noxafil;posaconazole;posaconazole hydrate;SCH 56592;SCH-56592

Chemical Property of Posaconazole

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 8.76E-31mmHg at 25°C
• Melting Point: 170-172 °C
• Refractive Index: 1.657
• Boiling Point: 850.7 °C at 760 mmHg
• PKA: 14.72±0.20(Predicted)
• Flash Point: 468.3 °C
• PSA: 115.70000
• Density: 1.36 g/cm³
• LogP: 4.70320
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 12
• Exact Mass: 700.32970817
• Heavy Atom Count: 51
• Complexity: 1170

Purity/Quality:

99% ^*data from raw suppliers

Posaconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antifungal Agents
• Canonical SMILES: CCC(C(C)O)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5CC(OC5)(CN6C=NC=N6)C7=C(C=C(C=C7)F)F
• Isomeric SMILES: CC[C@@H]([C@H](C)O)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OC[C@H]5C[C@](OC5)(CN6C=NC=N6)C7=C(C=C(C=C7)F)F
• Recent ClinicalTrials: Study of ABT-199 (GDC-0199) in Combination With Azacitidine or Decitabine (Chemo Combo) in Subjects With Acute Myelogenous Leukemia (AML)
• Recent EU Clinical Trials: Phase I / II, open label, dose escalation part (phase I) followed by non-comparative expansion part (phase II), multi-centre study, evaluating safety, pharmacokinetics and efficacy of S65487, a Bcl2 inhibitor combined with azacitidine in adult patients with previously untreated acute myeloid leukemia not eligible for intensive treatment
• General Description: Posaconazole is a triazole antifungal agent used to treat invasive fungal infections, and its synthesis can be optimized through a novel Pd0-catalyzed mono N-arylation of piperazine, which provides a more efficient and scalable route by avoiding harsh conditions and hazardous intermediates. This method enhances the production of key intermediates, such as N-(4-hydroxyphenyl)-N'(4-aminophenyl)piperazine, facilitating the synthesis of posaconazole with improved selectivity and yield.

Technology Process of Posaconazole

There total 74 articles about Posaconazole 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: 95.8%

C38H42F2N8O5 → posaconazote (171228-49-2)

Guidance literature:

With triethylamine; In methanol; at 60 - 70 ℃; for 1h; Reagent/catalyst; Temperature; Solvent;

Reference yield: 95.0%

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 (170985-86-1) → posaconazote (171228-49-2)

Guidance literature:

With hydrogenchloride; water; at 25 - 63 ℃; Temperature;

Reference yield: 90.0%

C37H44F2N8O5 (1350560-57-4) → posaconazote (171228-49-2)

Guidance literature:

With sodium hydroxide; In water; isopropyl alcohol; for 3h; Solvent; Reagent/catalyst; Time; Temperature; Reflux;

upstream raw materials:

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

2-((1S,2S)-2-Benzyloxymethoxy-1-ethyl-propyl)-4-[4-(4-{4-[(3R,5R)-5-(2,4-difluoro-phenyl)-5-[1,2,4]triazol-1-ylmethyl-tetrahydro-furan-3-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2,4-dihydro-[1,2,4]triazol-3-one

(2S,3R)-2-Benzyloxymethoxy-pentan-3-ol

4-Bromo-benzenesulfonic acid (1R,2S)-2-benzyloxymethoxy-1-ethyl-propyl ester

Downstream raw materials:

4-Benzyloxy-butyric acid (1S,2S)-2-{4-[4-(4-{4-[(3R,5R)-5-(2,4-difluoro-phenyl)-5-[1,2,4]triazol-1-ylmethyl-tetrahydro-furan-3-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-1-methyl-butyl ester

C₄₁H₄₇BrF₂N₈O₅

C₄₁H₄₆F₂N₈O₈

C₄₅H₅₇F₂N₉O₆

Refernces

Mono N-arylation of piperazine(III): Metal-catalyzed N-arylation and its application to the novel preparations of the antifungal posaconazole and its advanced intermediate

10.1016/S0040-4039(02)00556-7

The research focuses on the development of a novel Pd0-catalyzed method for the mono N-arylation of piperazine, a key intermediate in the synthesis of various biologically active compounds, including antifungal agents such as posaconazole. The study explores the mechanism behind this reaction and its application in the synthesis of the antifungal intermediate N-(4-hydroxyphenyl)-N'(4-aminophenyl)piperazine 5 and posaconazole 1. Experiments involved the use of various arylhalides with different electron-donating groups and steric hindrances to optimize the reaction conditions for high yields of mono N-arylated piperazines. Analytical techniques such as NMR were employed to study the reaction mechanism and catalyst deactivation. The research successfully demonstrated a mild, selective method for mono N-arylation, avoiding the use of carcinogenic intermediates, high pressure/temperature conditions, and chromatographic purifications, leading to a more efficient and scalable synthesis of the antifungal intermediates.

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