(R)-3-(1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide

Base Information

• Chemical Name: (R)-3-(1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide
• CAS No.: 1403883-46-4
• Molecular Formula: C₁₅H₁₀ClF₂N₃O₃S
• Molecular Weight: 385.779
• Mol file: 1403883-46-4.mol

Synonyms:(R)-3-(1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide

Chemical Property of (R)-3-(1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide

There total 6 articles about (R)-3-(1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide 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: 15.0%

(R)-3-(2-(benzyloxy)-1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)ethoxy)-2,6-difluorobenzonitrile (1403884-25-2) → (R)-3-(1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide (1403883-46-4)

Guidance literature:

(R)-3-(2-(benzyloxy)-1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)ethoxy)-2,6-difluorobenzonitrile; With sulfuric acid; at 60 ℃; for 0.5h;

With sodium hydroxide; In water; Cooling with ice;

Reference yield:

(R)-3-(benzyloxy)-2-(3-carbamoyl-2,4-difluorophenoxy)propanoic acid (1403884-21-8) → (R)-3-(1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide (1403883-46-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 20 °C / Cooling with ice

2.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice

3.1: oxalyl dichloride / N,N-dimethyl-formamide / acetonitrile / 0.5 h / 20 °C / Cooling with ice

4.1: tetraphosphorus decasulfide / toluene / 1 h / Reflux

5.1: sulfuric acid / 0.5 h / 60 °C

5.2: Cooling with ice

With tetraphosphorus decasulfide; oxalyl dichloride; sulfuric acid; triethylamine; N,N-dimethyl-formamide; In dichloromethane; toluene; acetonitrile;

Reference yield:

(R)-3-benzyloxy-2-(3-carbamoyl-2,4-difluoro-phenoxy)propionic acid methyl ester (1403884-02-5) → (R)-3-(1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide (1403883-46-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 20 °C

1.2: pH 4

2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 20 °C / Cooling with ice

3.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice

4.1: oxalyl dichloride / N,N-dimethyl-formamide / acetonitrile / 0.5 h / 20 °C / Cooling with ice

5.1: tetraphosphorus decasulfide / toluene / 1 h / Reflux

6.1: sulfuric acid / 0.5 h / 60 °C

6.2: Cooling with ice

With tetraphosphorus decasulfide; oxalyl dichloride; sulfuric acid; water; triethylamine; lithium hydroxide; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

upstream raw materials:

(R)-3-(2-(benzyloxy)-1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)ethoxy)-2,6-difluorobenzonitrile

(R)-3-benzyloxy-2-(3-carbamoyl-2,4-difluoro-phenoxy)propionic acid methyl ester

(R)-3-(benzyloxy)-2-(3-carbamoyl-2,4-difluorophenoxy)propanoic acid

(R)-3-(benzyloxy)-2-(3-carbamoyl-2,4-difluorophenoxy)propanoyl chloride

Refernces