Vilanterol

Base Information

• Chemical Name: Vilanterol
• CAS No.: 503068-34-6
• Molecular Formula: C24H33Cl2NO5
• Molecular Weight: 486.436
• European Community (EC) Number: 690-631-3
• UNII: 028LZY775B
• DSSTox Substance ID: DTXSID80198318
• Nikkaji Number: J3.221.142I
• Wikipedia: Vilanterol
• Wikidata: Q15053666
• NCI Thesaurus Code: C152875
• RXCUI: 1424884
• Pharos Ligand ID: WUNN6U3AP4Z8
• Metabolomics Workbench ID: 152136
• ChEMBL ID: CHEMBL1198857
• Mol file: 503068-34-6.mol

Synonyms:4-(2-((6-((2-(((2,6-dichlorophenyl)methyl)oxy)ethyl)oxy)hexyl)amino)-1-hydroxyethyl)-2-(hydroxymethyl)phenol;vilanterol

Chemical Property of Vilanterol

Chemical Property:

• Boiling Point: 646.7±55.0 °C(Predicted)
• PKA: 9.99±0.20(Predicted)
• PSA: 91.18000
• Density: 1 +-.0.06 g/cm3(Predicted)
• LogP: 4.99900
• Solubility.: Soluble in DMSO
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 16
• Exact Mass: 485.1735785
• Heavy Atom Count: 32
• Complexity: 466

Purity/Quality:

99%, ^*data from raw suppliers

Vilanterol 96.66% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Cl)COCCOCCCCCCNCC(C2=CC(=C(C=C2)O)CO)O)Cl
• Isomeric SMILES: C1=CC(=C(C(=C1)Cl)COCCOCCCCCCNC[C@@H](C2=CC(=C(C=C2)O)CO)O)Cl
• Recent ClinicalTrials: A Study in the US Based on Pharmacy and Medical Claims That Compares How Well Stiolto? and Trelegy? Work in People With Chronic Obstructive Pulmonary Disease (COPD)
• Recent EU Clinical Trials: An open label, randomised, parallel group clinical study to evaluate the effect of the Connected Inhaler System (CIS) on adherence to Relvar/Breo ELLIPTA therapy, in asthmatic subjects with poor control.
• Recent NIPH Clinical Trials: Efficacy and safety of once-daily single-Inhaler TRiple (Trelegy Ellipta) therApy for Japanese with mild to moderate COPD in Kyushu (TRACK study)

Technology Process of Vilanterol

There total 25 articles about Vilanterol 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: 88.0%

C24H31Cl2NO6 → 4-[(1R)-2-({6-[(2-{[(2,6-dichlorophenyl)methyl]oxy}ethyl)oxy]-hexyl}-amino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol (503068-34-6)

Guidance literature:

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 ℃; for 4.66667h; Inert atmosphere; Reflux;

Reference yield:

(R)-2-{6-[2-(2,6-dichlorobenzyloxy)ethoxy]hexylamino}-1-(2 ,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)ethanol succinate → 4-[(1R)-2-({6-[(2-{[(2,6-dichlorophenyl)methyl]oxy}ethyl)oxy]-hexyl}-amino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol (503068-34-6)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; at 5 - 20 ℃; for 4h; Solvent; Reagent/catalyst;

Reference yield:

2-((2-((6-bromohexyl)oxy)ethoxy)methyl)-1,3-dichlorobenzene (503070-57-3) → 4-[(1R)-2-({6-[(2-{[(2,6-dichlorophenyl)methyl]oxy}ethyl)oxy]-hexyl}-amino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol (503068-34-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

1.2: 3 h / 20 °C / Inert atmosphere

2.1: potassium trimethylsilonate / tetrahydrofuran / 2 h / 60 - 65 °C / Inert atmosphere

3.1: water; hydrogenchloride / acetone / 1 h / 0 - 5 °C / Inert atmosphere

With hydrogenchloride; potassium tert-butylate; potassium trimethylsilonate; water; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

upstream raw materials:

1-(2,2-dimethyl-4H-benzo[d][1,3]dioxan-6-yl)ethanone

2-bromo-1-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)ethanone

di-(tert-butyl) 2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxoethyliminodicarbonate

tert-butyl 2-(2,2-dimethyl-4H-1,3-benzodioxane-6-yl)-2-carbonylethylcarbamate

Downstream raw materials:

4‐{(1R)‐2‐[(6‐{2‐[(2,6‐dichlorobenzyl)oxy]ethoxy}hexyl)amino]‐1‐hydroxyethyl}‐2‐(hydroxymethyl)phenol triphenylacetate

4-[(1R)-2-({6-[(2-{[(2,6-dichlorophenyl)methyl]oxy}ethyl)oxy]-hexyl}-amino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol α-phenylcinnamate

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR PREPARATION OF VILANTEROL OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF". . . Retrieved 2021/02/26.
• 2、 -. "Preparation method of vilanterol and salt thereof". . . Retrieved 2020/11/02.