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

Base Information

• Chemical Name: 2-sec-Butyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2H-1,2,4-triazol-3(4H)-one
• CAS No.: 252964-68-4
• Molecular Formula: C23H29N5O2
• Molecular Weight: 407.516
• European Community (EC) Number: 607-685-0
• UNII: 148K9U451A
• ChEMBL ID: CHEMBL1521638
• DSSTox Substance ID: DTXSID501021088
• Nikkaji Number: J3.273.712I
• Wikidata: Q27251604
• Mol file: 252964-68-4.mol

Synonyms:252964-68-4;2-(2-Butyl)-4-{4-[4-(4-methyloxy-phenyl)-piperazin-1-yl]-phenyl}-2,4-dihydro-[1,2,4]-triazol-3-one;2-sec-Butyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2H-1,2,4-triazol-3(4H)-one;2,4-Dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one;2-butan-2-yl-4-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-1,2,4-triazol-3-one;1-(sec-Butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one;148K9U451A;3H-1,2,4-Triazol-3-one, 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-;2-sec-Butyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2H-1,2,4-triazol-3(4H)-one, (RS)-;3H-1,2,4-Triazol-3-one, 2,4-dihydro-4-(4-(4-(4-methoxyphenyl)-1-piperazinyl)phenyl)-2-(1-methylpropyl)-;4-(4-(4-(4-Methoxyphenyl)piperazin-1-yl)phenyl)-2-((1RS)-1-methylpropyl)-2,4-dihydro-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;2-sec-Butyl-4-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl-2,4-dihydro-[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;Itraconazole impurity A [EP];UNII-148K9U451A;trolnitratephosphate;4-[4-[4-(4-METHOXYPHENYL)PIPERAZIN-1-YL]PHENYL]-2-[(1RS)-1-METHYLPROPYL]-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE;4-[4-[4-(4-Methoxyphenyl)piperazin-1-yl]phenyl]-2-[(1RS)-1-methylpropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one;Itraconazole Imp. A (EP);Itraconazole Impurity A;TimTec1_006484;Oprea1_708999;MLS000703920;Itraconazole impurity, 4-methoxy derivative- [USP];SCHEMBL2548018;CHEMBL1521638;Itraconazole 4-Methoxy Derivative;IVIVGYTUQVJVPF-UHFFFAOYSA-N;DTXSID501021088;HMS1552G16;HMS2525K04;AKOS015965312;4-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-2-sec-butyl-1,2,4-triazol-3-one;AC-20416;AS-40212;SMR000229838;CS-0328221;FT-0664144;FT-0664145;ITRACONAZOLE IMPURITY A [EP IMPURITY];A817769;AP-312/40633640;A1-01735;Q27251604;ITRACONAZOLE IMPURITY, 4-METHOXY DERIVATIVE- [USP IMPURITY];1-Sec butyl-[4[4(4-methoxyphenyl)-1-piperazinyl]phenyl]-1,2,4-triazolo-5-one;1-sec-butyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one;1-(butan-2-yl)-4-{4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one;2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]-phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one;2-(2-Butyl)-4-{4-[4-(4-methyloxy-phenyl)-piperazin-1-yl]-phenyl}-2,4-dihydr o-[1,2,4]-triazol-3-one

Chemical Property of 2-sec-Butyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2H-1,2,4-triazol-3(4H)-one

Chemical Property:

• Vapor Pressure: 4.12E-13mmHg at 25°C
• Melting Point: 189-191 °C
• Refractive Index: 1.622
• Boiling Point: 572.4 °C at 760 mmHg
• PKA: 6.57±0.40(Predicted)
• Flash Point: 300 °C
• PSA: 55.53000
• Density: 1.2g/cm³
• LogP: 3.47020
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 407.23212518
• Heavy Atom Count: 30
• Complexity: 590

Purity/Quality:

99.9% ^*data from raw suppliers

2-(2-Butyl)-4-{4-[4-(4-methyloxy-phenyl)-piperazin-1-yl]-phenyl}-2,4-dihydro-[1,2,4]-triazol-3-one ^*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)OC
• Uses: An intermediate of Itraconazole.

Technology Process of 2-sec-Butyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2H-1,2,4-triazol-3(4H)-one

There total 7 articles about 2-sec-Butyl-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2H-1,2,4-triazol-3(4H)-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: 89.0%

N'-sec-butylformohydrazide (939027-86-8) + phenyl (4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate (74853-06-8) → 2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (252964-68-4)

Guidance literature:

N'-sec-butylformohydrazide; phenyl (4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 80 ℃; for 15.5h; Heating / reflux;

With methanol; In toluene; at 4 - 20 ℃; for 2h;

Reference yield: 67.0%

s-butyl bromide (78-76-2,5787-31-5) + 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one (74853-07-9) → 2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (252964-68-4)

Guidance literature:

With 18-crown-6 ether; for 12h;

Reference yield:

4-(4-methoxyphenyl)piperazine (38212-30-5) → 2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (252964-68-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / dimethyl sulfoxide / 160 °C

2.1: ammonium formate / palladium 10% on activated carbon / methanol / 3 h / Heating / reflux

3.1: pyridine / dichloromethane / 0 - 4 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 15.5 h / 80 °C / Heating / reflux

4.2: 2 h / 4 - 20 °C

With pyridine; ammonium formate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium 10% on activated carbon; In methanol; dichloromethane; dimethyl sulfoxide; toluene;

upstream raw materials:

N'-sec-butylformohydrazide

phenyl (4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate

4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenylamine

butan-2-one formylhydrazone

Downstream raw materials:

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

(2S,4R)-itraconazole

itraconazole