2-[(2r)-Butan-2-Yl]-4-{4-[4-(4-{[(2r,4s)-2-(2,4-Dichlorophenyl)-2-(1h-1,2,4-Triazol-1-Ylmethyl)-1,3-Dioxolan-4-Yl]methoxy}phenyl)piperazin-1-Yl]phenyl}-2,4-Dihydro-3h-1,2,4-Triazol-3-One

Base Information

• Chemical Name: 2-[(2r)-Butan-2-Yl]-4-{4-[4-(4-{[(2r,4s)-2-(2,4-Dichlorophenyl)-2-(1h-1,2,4-Triazol-1-Ylmethyl)-1,3-Dioxolan-4-Yl]methoxy}phenyl)piperazin-1-Yl]phenyl}-2,4-Dihydro-3h-1,2,4-Triazol-3-One
• CAS No.: 154003-17-5
• Molecular Formula: C35H38Cl2N8O4
• Molecular Weight: 705.644
• European Community (EC) Number: 617-596-9
• UNII: R67CDS9QK4
• ChEMBL ID: CHEMBL1835951
• Nikkaji Number: J3.033.099D
• Wikidata: Q27452583
• Wikipedia: Itraconazole
• Mol file: 154003-17-5.mol

Synonyms:R67CDS9QK4;Itraconazole, (S)-(+)-;CHEMBL1835951;154003-17-5;2-[(2r)-Butan-2-Yl]-4-{4-[4-(4-{[(2r,4s)-2-(2,4-Dichlorophenyl)-2-(1h-1,2,4-Triazol-1-Ylmethyl)-1,3-Dioxolan-4-Yl]methoxy}phenyl)piperazin-1-Yl]phenyl}-2,4-Dihydro-3h-1,2,4-Triazol-3-One;2-[(2R)-butan-2-yl]-4-[4-[4-[4-[[(2R,4S)-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;84625-61-6;3H-1,2,4-Triazol-3-one, 4-(4-(4-(4-(((2R,4S)-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-((1R)-1-methylpropyl)-;3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[(2R,4S)-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-[(1R)-1-methylpropyl]-;4-(4-(4-(4-(((2R,4S)-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-((1R)-1-methylpropyl)-3H-1,2,4-triazol-3-one;4-[4-[4-[4-[[(2R,4S)-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-[(1R)-1-methylpropyl]-3H-1,2,4-triazol-3-one;UNII-R67CDS9QK4;SCHEMBL64913;BDBM50088483;Q27452583

Chemical Property of 2-[(2r)-Butan-2-Yl]-4-{4-[4-(4-{[(2r,4s)-2-(2,4-Dichlorophenyl)-2-(1h-1,2,4-Triazol-1-Ylmethyl)-1,3-Dioxolan-4-Yl]methoxy}phenyl)piperazin-1-Yl]phenyl}-2,4-Dihydro-3h-1,2,4-Triazol-3-One

Chemical Property:

• 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:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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: CC[C@@H](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
• Recent EU Clinical Trials: Covid-19: A randomized, open-label, adaptive, proof-of- concept clinical trial of new antiviral drug candidates against SARS-CoV-2.

Technology Process of 2-[(2r)-Butan-2-Yl]-4-{4-[4-(4-{[(2r,4s)-2-(2,4-Dichlorophenyl)-2-(1h-1,2,4-Triazol-1-Ylmethyl)-1,3-Dioxolan-4-Yl]methoxy}phenyl)piperazin-1-Yl]phenyl}-2,4-Dihydro-3h-1,2,4-Triazol-3-One

There total 6 articles about 2-[(2r)-Butan-2-Yl]-4-{4-[4-(4-{[(2r,4s)-2-(2,4-Dichlorophenyl)-2-(1h-1,2,4-Triazol-1-Ylmethyl)-1,3-Dioxolan-4-Yl]methoxy}phenyl)piperazin-1-Yl]phenyl}-2,4-Dihydro-3h-1,2,4-Triazol-3-One 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: 62.0%

(R)-2-(sec-butyl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (125235-74-7) + (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'S)-Itraconazole (154003-17-5,252964-65-1,873066-43-4)

Guidance literature:

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

DOI:10.1021/ml1000068

Reference yield:

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (58905-16-1) → (2R,4S,2'S)-Itraconazole (154003-17-5,252964-65-1,873066-43-4)

Guidance literature:

Multi-step reaction with 5 steps

1: methanesulfonic acid / toluene / 4 h / 40 °C

2: 1-methyl-pyrrolidin-2-one / 10 h / 120 °C

3: lithium hydroxide / ethanol / 3 h / 25 °C

4: triethylamine / dichloromethane / 5 h / -20 - 25 °C

5: potassium hydroxide / N,N-dimethyl-formamide / 20 h / 30 - 40 °C

With methanesulfonic acid; triethylamine; potassium hydroxide; lithium hydroxide; In 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

itraconazole (84604-65-9,84625-61-6,252964-65-1,873066-43-4) → (2R,4S,2'S)-Itraconazole (154003-17-5,252964-65-1,873066-43-4) + (2R,4S,2'R)-Itraconazole (154003-18-6,252964-65-1,873066-43-4) + (2S,4R,2'S)-Itraconazole (154003-19-7,252964-65-1,873066-43-4) + (2S,4R,2'R)-Itraconazole (154003-20-0,252964-65-1,873066-43-4)

Guidance literature:

With Chiralcel OD chiral stationary phase; In ethanol; hexane; isopropyl alcohol; acetonitrile; at 40 ℃; stereoselective reaction; Resolution of racemate;

DOI:10.1002/chir.20932

upstream raw materials:

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

(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-4-tozyloxymethyl-1,3-dioxolane

itraconazole

Benzoic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester