GSK2190915

Base Information

• Chemical Name: GSK2190915
• CAS No.: 936350-00-4
• Molecular Formula: C₃₈H₄₃N₃O₄S
• Molecular Weight: 637.843
• Mol file: 936350-00-4.mol

Synonyms:GSK2190915;GSK2190915 (AM803);fiboflapon;AM 803;3-[(1,1-Dimethylethyl)thio]-1-[[4-(6-ethoxy-3-pyridinyl)phenyl]methyl]-alpha,alpha-dimethyl-5-[(5-methyl-2-pyridinyl)methoxy]-1H-indole-2-propanoic acid

Chemical Property of GSK2190915

Chemical Property:

• Boiling Point: 796.3±60.0 °C(Predicted)
• PKA: 4.70±0.10(Predicted)
• PSA: 111.77000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: 8.97660

Purity/Quality:

97% ^*data from raw suppliers

Fiboflapon 98.18% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of GSK2190915

There total 18 articles about GSK2190915 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: 97.7%

3-[3-tert-butylsulfanyl-1-[4-(6-ethoxy-pyridin-3-yl)-benzyl]-5-(5-methyl-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester (1196965-16-8) → 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxy-pyridin-3-yl)-benzyl]-5-(5-methyl-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid (936350-00-4)

Guidance literature:

3-[3-tert-butylsulfanyl-1-[4-(6-ethoxy-pyridin-3-yl)-benzyl]-5-(5-methyl-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester; With water; sodium hydroxide; In tetrahydrofuran; ethanol; Reflux; Industry scale;

With hydrogenchloride; In tetrahydrofuran; water; pH=4; Industry scale;

Reference yield: 76.0%

2-(ethyloxy)-5-(4-{[1-(4-{[(5-methylpyridin-2-yl)methyl]oxy}phenyl)hydrazino]methyl}phenyl)pyridine (1300640-30-5) + ethyl 5-t-butylthio-2,2-dimethyl-4-oxo-pentanoate (136558-13-9) → 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxy-pyridin-3-yl)-benzyl]-5-(5-methyl-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid (936350-00-4)

Guidance literature:

2-(ethyloxy)-5-(4-{[1-(4-{[(5-methylpyridin-2-yl)methyl]oxy}phenyl)hydrazino]methyl}phenyl)pyridine; ethyl 5-t-butylthio-2,2-dimethyl-4-oxo-pentanoate; With rac-tartaric acid dibenzoate; citric acid; In 2-methyltetrahydrofuran; at 30 - 55 ℃; for 21h; Industry scale; Inert atmosphere;

With water; sodium hydroxide; In 2-methyltetrahydrofuran; for 1h; Industry scale;

With hydrogenchloride; In 2-methyltetrahydrofuran; water; Product distribution / selectivity; Industry scale;

Reference yield:

p-hydroxymethylphenylboronic acid (59016-93-2) → 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxy-pyridin-3-yl)-benzyl]-5-(5-methyl-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid (936350-00-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium carbonate / palladium 10% on activated carbon / ethanol; water / 5 h / 63 °C / Industry scale; Inert atmosphere; Reflux

2.1: hydrogen bromide; acetic acid / 4 h / 45 - 55 °C / Industry scale

3.1: hydrogenchloride; sodium nitrite / water / 0 - 5 °C

3.2: 0.17 h / 10 - 25 °C / pH 7 / Inert atmosphere

3.3: 18 °C

4.1: citric acid; rac-tartaric acid dibenzoate / 2-methyltetrahydrofuran / 21 h / 30 - 55 °C / Industry scale; Inert atmosphere

4.2: 1 h / Industry scale

4.3: Industry scale

With hydrogenchloride; rac-tartaric acid dibenzoate; hydrogen bromide; sodium carbonate; acetic acid; citric acid; sodium nitrite; palladium 10% on activated carbon; In 2-methyltetrahydrofuran; ethanol; water;

upstream raw materials:

3-[3-tert-butylsulfanyl-1-[4-(6-ethoxy-pyridin-3-yl)-benzyl]-5-(5-methyl-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester

2,5-dimethylpyridine N-oxide

3-[1-(4-bromo-benzyl)-3-tert-butylsulfanyl-5-hydroxy-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester

2-acetoxymethyl-5-methyl pyridine