(2S)-methyl 2-(((11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (2S)-methyl 2-(((11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate
• CAS No.: 1427033-56-4
• Molecular Formula: C₄₀H₃₆F₂N₆O₈S
• Molecular Weight: 798.824
• Mol file: 1427033-56-4.mol

Synonyms:(2S)-methyl 2-(((11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate

Chemical Property of (2S)-methyl 2-(((11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-methyl 2-(((11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate

There total 24 articles about (2S)-methyl 2-(((11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate 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: 69.0%

5-(6-(aminomethyl)-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1427034-97-6) + (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid (74761-41-4,134250-76-3) → (2S)-methyl 2-(((11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate (1427033-56-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃;

Reference yield:

6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-ol (1426942-84-8) → (2S)-methyl 2-(((11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate (1427033-56-4)

Guidance literature:

Multi-step reaction with 9 steps

1: hydrogenchloride; tin / ethanol / 3 h / Reflux

2: methanesulfonic acid / tetrahydrofuran / 2 h / 50 °C

3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / 80 °C

4: sodium tetrahydroborate / dichloromethane; methanol / 2 h / 20 °C

5: pyridine / 2 h / 0 - 20 °C / Inert atmosphere

6: sodium azide / N,N-dimethyl-formamide / 6 h / 60 °C / Inert atmosphere

7: XPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere

8: hydrogen; 5%-palladium/activated carbon / methanol / 20 °C / 1551.49 Torr

9: triethylamine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

With pyridine; hydrogenchloride; dmap; tin; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium azide; methanesulfonic acid; potassium phosphate tribasic trihydrate; 5%-palladium/activated carbon; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; XPhos; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

ethyl 2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole-6-carboxylate (1427034-84-1) → (2S)-methyl 2-(((11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate (1427033-56-4)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium tetrahydroborate / dichloromethane; methanol / 2 h / 20 °C

2: pyridine / 2 h / 0 - 20 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 6 h / 60 °C / Inert atmosphere

4: XPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere

5: hydrogen; 5%-palladium/activated carbon / methanol / 20 °C / 1551.49 Torr

6: triethylamine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

With pyridine; dmap; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium azide; potassium phosphate tribasic trihydrate; 5%-palladium/activated carbon; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; XPhos; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-ol

6-chloro-2-(4-fluoroindolin-2-yl)pyridin-3-ol

ethyl 2-chloro-11-fluoro-12,12a-dihydro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole-6-carboxylate

ethyl 2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole-6-carboxylate

Refernces

• 1、 -. "TETRACYCLIC HETEROCYCLE COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES". . . Retrieved 2013/03/26.