trans-Itraconazole

Base Information

• Chemical Name: trans-Itraconazole
• CAS No.: 252964-65-1
• Molecular Formula: C₃₅H₃₈Cl₂N₈O₄
• Molecular Weight: 705.644
• UNII: DQ63FB41CJ
• DSSTox Substance ID: DTXSID40861071
• Nikkaji Number: J2.113.296I
• Wikidata: Q27276530
• Mol file: 252964-65-1.mol

Synonyms:trans-Itraconazole;252964-65-1;Itraconazole Impurity E;Itraconazole, trans-;Itraconazole, trans- (+/-)-;DQ63FB41CJ;2-butan-2-yl-4-[4-[4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one;3H-1,2,4-Triazol-3-one, 4-(4-(4-(4-(((2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-2,4-dihydro-2-(1-methylpropyl)-, rel-;4-(4-(4-(4-(((2RS,4RS)-2-((1H-1,2,4-Triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-sec-butyl-2H-1,2,4-triazol-3(4H)-one;UNII-DQ63FB41CJ;Itraconazole impurity, epimer- [USP];Itraconazole specified impurity E [EP];DTXSID40861071;ITRACONAZOLE IMPURITY E [EP IMPURITY];(2R,4R)-Itraconazole (Mixture of Diastereomers);ITRACONAZOLE IMPURITY, EPIMER- [USP IMPURITY];Q27276530;2-butan-2-yl-4-[4-[4-[4-[[(2R, 4R)-2-(2, 4-dichlorophenyl)-2-(1, 2, 4-triazol-1-ylmethyl)-1, 3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1, 2, 4-triazol-3-one

Chemical Property of trans-Itraconazole

Chemical Property:

• Boiling Point: 850.0±75.0 °C(Predicted)
• PKA: 6.47±0.40(Predicted)
• PSA: 104.70000
• Density: 1.40±0.1 g/cm3(Predicted)
• LogP: 5.70730
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 704.2393071
• Heavy Atom Count: 49
• Complexity: 1120

Purity/Quality:

97% ^*data from raw suppliers

trans-Itraconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5COC(O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl
• Isomeric SMILES: CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OC[C@@H]5CO[C@](O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl
• Uses: trans-Itraconazole (Itraconazole EP Impurity E) is a geometrical isomer of Itraconazole (I937500). It is a COVID19-related research product. A geometrical isomer of Itraconazole (I937500).

Technology Process of trans-Itraconazole

There total 57 articles about trans-Itraconazole 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: 90.5%

(-)-(R)-2,4dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol 3-one (106461-41-0) + Toluene-4-sulfonic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester (113770-65-3) → itraconazole (84625-61-6,252964-65-1,873066-43-4)

Guidance literature:

(-)-(R)-2,4dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol 3-one; With hydrazine hydrate; sodium hydroxide; In N,N-dimethyl-formamide; at 40 ℃; for 0.666667h; Inert atmosphere;

Toluene-4-sulfonic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester; In N,N-dimethyl-formamide; at 60 ℃; for 1.5h;

Reference yield: 69.0%

(-)-(R)-2,4dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol 3-one (106461-41-0) + 2RS,4RS-toluene-4-sulfonic acid (2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)methyl-1,3-dioxolan-4-yl)methyl ester (113770-65-3) → itraconazole (84604-65-9,84625-61-6,252964-65-1,873066-43-4)

Guidance literature:

With caesium carbonate; In dimethyl sulfoxide; at 80 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b01718

Reference yield: 62.0%

(S)-2-(sec-butyl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (125235-31-6) + (2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-4-tozyloxymethyl-1,3-dioxolane (154003-23-3,113770-65-3) → (2R,4S,2'R)-Itraconazole (154003-18-6,252964-65-1,873066-43-4)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; at 50 - 85 ℃;

DOI:10.1021/ml1000068

upstream raw materials:

2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one

2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

(-)-(R)-2,4dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol 3-one

2RS,4RS-toluene-4-sulfonic acid (2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)methyl-1,3-dioxolan-4-yl)methyl ester