N-(3-((3-(9H-purin-6-yl)pyridin-2-yl)amino)-2,4-difluorophenyl)thiophene-2-sulfonamide

Base Information

• Chemical Name: N-(3-((3-(9H-purin-6-yl)pyridin-2-yl)amino)-2,4-difluorophenyl)thiophene-2-sulfonamide
• CAS No.: 1380228-02-3
• Molecular Formula: C₂₀H₁₃F₂N₇O₂S₂
• Molecular Weight: 485.498
• Mol file: 1380228-02-3.mol

Synonyms:N-(3-((3-(9H-purin-6-yl)pyridin-2-yl)amino)-2,4-difluorophenyl)thiophene-2-sulfonamide

Chemical Property of N-(3-((3-(9H-purin-6-yl)pyridin-2-yl)amino)-2,4-difluorophenyl)thiophene-2-sulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(3-((3-(9H-purin-6-yl)pyridin-2-yl)amino)-2,4-difluorophenyl)thiophene-2-sulfonamide

There total 21 articles about N-(3-((3-(9H-purin-6-yl)pyridin-2-yl)amino)-2,4-difluorophenyl)thiophene-2-sulfonamide 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: 81.0%

N-(2,4-difluoro-3-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)phenyl)thiophene-2-sulfonamide (1380228-78-3) → N-(3-((3-(9H-purin-6-yl)pyridin-2-yl)amino)-2,4-difluorophenyl)thiophene-2-sulfonamide (1380228-02-3)

Guidance literature:

N-(2,4-difluoro-3-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)phenyl)thiophene-2-sulfonamide; With hydrogenchloride; In water; for 2h;

With sodium carbonate; In water;

Reference yield:

tert-butyl (2,6-difluoro-3-nitrophenyl)carbamate (535170-17-3) → N-(3-((3-(9H-purin-6-yl)pyridin-2-yl)amino)-2,4-difluorophenyl)thiophene-2-sulfonamide (1380228-02-3)

Guidance literature:

Multi-step reaction with 7 steps

1: palladium on activated charcoal; hydrogen / methanol / 15 h

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 20 °C

3: hydrogenchloride / ethyl acetate; 1,4-dioxane / 5 h / 20 °C

4: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C

5: palladium on activated charcoal; hydrogen / methanol / 1 h

6: pyridine / dichloromethane / 2 h / 50 °C

7: hydrogenchloride / water / 2 h

With pyridine; hydrogenchloride; palladium on activated charcoal; hydrogen; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate;

Reference yield:

2,6-difluorobenzoic acid (385-00-2) → N-(3-((3-(9H-purin-6-yl)pyridin-2-yl)amino)-2,4-difluorophenyl)thiophene-2-sulfonamide (1380228-02-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sulfuric acid; potassium nitrate / 24 h / 0 - 20 °C

2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 18 h / 20 °C

3.1: sodium azide / dichloromethane / 0.5 h / 20 °C

3.2: 3 h / Reflux

4.1: palladium on activated charcoal; hydrogen / methanol / 15 h

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 20 °C

6.1: hydrogenchloride / ethyl acetate; 1,4-dioxane / 5 h / 20 °C

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C

8.1: palladium on activated charcoal; hydrogen / methanol / 1 h

9.1: pyridine / dichloromethane / 2 h / 50 °C

10.1: hydrogenchloride / water / 2 h

With pyridine; hydrogenchloride; sodium azide; oxalyl dichloride; sulfuric acid; palladium on activated charcoal; hydrogen; potassium nitrate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate;

upstream raw materials:

tert-butyl (2,6-difluoro-3-nitrophenyl)carbamate

6-chloropurine

6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

6-(2-fluoropyridin-3-yl)-9-(tetrahydro-2-hydro-pyran-2-yl)-9H-purine

Refernces

• 1、 Liu, Longbin,Lee, Matthew R.,Kim, Joseph L.,Whittington, Douglas A.,Bregman, Howard,Hua, Zihao,Lewis, Richard T.,Martin, Matthew W.,Nishimura, Nobuko,Potashman, Michele,Yang, Kevin,Yi, Shuyan,Vaida, Karina R.,Epstein, Linda F.,Babij, Carol,Fernando, Manory,Carnahan, Josette,Norman, Mark H.. "Purinylpyridinylamino-based DFG-in/αC-helix-out B-Raf inhibitors: Applying mutant versus wild-type B-Raf selectivity indices for compound profiling". . p. 2215 - 2234. Retrieved 2016/04/26.