3-(5-Methylisoxazol-3-yl)-6-[(1-methyl-1H-1,2,3-triazol-4-yl)methoxy][1,2,4]triazolo[3,4-a]phthalazine

Base Information

• Chemical Name: 3-(5-Methylisoxazol-3-yl)-6-[(1-methyl-1H-1,2,3-triazol-4-yl)methoxy][1,2,4]triazolo[3,4-a]phthalazine
• CAS No.: 215874-86-5
• Molecular Formula: C17H14N8O2
• Molecular Weight: 362.351
• Hs Code.: 2934999090
• UNII: 1M7NI1A92L
• DSSTox Substance ID: DTXSID10175950
• Nikkaji Number: J2.019.355G
• Wikipedia: %CE%915IA
• Wikidata: Q8083967
• Pharos Ligand ID: 2MURU7KUNWFT
• ChEMBL ID: CHEMBL306422
• Mol file: 215874-86-5.mol

Synonyms:3-(5-methylisoxazol-3-yl)-6-((1-methyl-1,2,3-triazol-4-yl)methyloxy)-1,2,4-triazolo(3,4-a)phthalazine;alpha5IA cpd

Chemical Property of 3-(5-Methylisoxazol-3-yl)-6-[(1-methyl-1H-1,2,3-triazol-4-yl)methoxy][1,2,4]triazolo[3,4-a]phthalazine

Chemical Property:

• PSA: 109.05000
• LogP: 1.94840
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >2mg/mL
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 362.12397172
• Heavy Atom Count: 27
• Complexity: 527

Purity/Quality:

99% ^*data from raw suppliers

Alpha5IA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=NO1)C2=NN=C3N2N=C(C4=CC=CC=C43)OCC5=CN(N=N5)C
• Uses: Alpha5IA is an α5-selective inverse agonist which enhance cognitive performance in rodents and encouraging in human. A triazolophthalazine that selectively attentuates the effects of GABA at GABAA receptors.

Technology Process of 3-(5-Methylisoxazol-3-yl)-6-[(1-methyl-1H-1,2,3-triazol-4-yl)methoxy][1,2,4]triazolo[3,4-a]phthalazine

There total 6 articles about 3-(5-Methylisoxazol-3-yl)-6-[(1-methyl-1H-1,2,3-triazol-4-yl)methoxy][1,2,4]triazolo[3,4-a]phthalazine 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: 61.0%

(1-methyl-1H-[1,2,3]triazol-4-yl)methanol (77177-21-0) + 6-chloro-3-(5-methylisoxazol-3-yl)-1,2,4-triazolo[3,4-a]phthalazine (215874-89-8) → 3-(5-methylisoxazol-3-yl)-6-[(1-methyl-1,2,3-triazol-4-yl)methyloxy]-1,2,4-triazolo[3–a]phthalazine (215874-86-5)

Guidance literature:

(1-methyl-1H-[1,2,3]triazol-4-yl)methanol; With lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at -10 ℃; for 0.5h;

6-chloro-3-(5-methylisoxazol-3-yl)-1,2,4-triazolo[3,4-a]phthalazine; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/jm031076j

Reference yield:

5-methylisoxazole 3-carboxylic acid (3405-77-4) → 3-(5-methylisoxazol-3-yl)-6-[(1-methyl-1,2,3-triazol-4-yl)methyloxy]-1,2,4-triazolo[3–a]phthalazine (215874-86-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 11 g / bis-2-oxo-3-oxazolidinyl phosphinic chloride; Et₃N / CH₂Cl₂ / 0 - 20 °C

2.1: 58 percent / Et₃N*HCl / xylene / 3 h / Heating

3.1: lithium bis(trimethylsilyl)amide / dimethylformamide; tetrahydrofuran / 0.5 h / -10 °C

3.2: 61 percent / dimethylformamide; tetrahydrofuran / 16 h / 20 °C

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine hydrochloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; xylene;

DOI:10.1021/jm031076j

Reference yield:

1,4-dichlorophthalazine (4752-10-7) → 3-(5-methylisoxazol-3-yl)-6-[(1-methyl-1,2,3-triazol-4-yl)methyloxy]-1,2,4-triazolo[3–a]phthalazine (215874-86-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / NH₂NH₂*H₂O; aq. NH₃ / ethanol / 0.17 h / Heating

2.1: 11 g / bis-2-oxo-3-oxazolidinyl phosphinic chloride; Et₃N / CH₂Cl₂ / 0 - 20 °C

3.1: 58 percent / Et₃N*HCl / xylene / 3 h / Heating

4.1: lithium bis(trimethylsilyl)amide / dimethylformamide; tetrahydrofuran / 0.5 h / -10 °C

4.2: 61 percent / dimethylformamide; tetrahydrofuran / 16 h / 20 °C

With ammonium hydroxide; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine hydrochloride; hydrazine hydrate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; xylene;

DOI:10.1021/jm031076j

upstream raw materials:

(1-methyl-1H-[1,2,3]triazol-4-yl)methanol

6-chloro-3-(5-methylisoxazol-3-yl)-1,2,4-triazolo[3,4-a]phthalazine

5-methylisoxazole 3-carboxylic acid

1,4-dichlorophthalazine

Refernces

• 1、 -. "Substituted 1,2,4-triazolo[3,4-a]phthalazine derivatives as GABA alpha 5 ligands". . . Retrieved 2008/06/13.