[(rac)-8-(3,4-difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[(rac)-8-endo-3-(3-methyl-[1,2,4]thiadiazol-5-yl)-3-aza-bicyclo[3.2.1]oct-8-yl]-amine

Base Information

• Chemical Name: [(rac)-8-(3,4-difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[(rac)-8-endo-3-(3-methyl-[1,2,4]thiadiazol-5-yl)-3-aza-bicyclo[3.2.1]oct-8-yl]-amine
• CAS No.: 1397287-23-8
• Molecular Formula: C₂₂H₂₅F₂N₇S
• Molecular Weight: 457.55
• Mol file: 1397287-23-8.mol

Synonyms:[(rac)-8-(3,4-difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[(rac)-8-endo-3-(3-methyl-[1,2,4]thiadiazol-5-yl)-3-aza-bicyclo[3.2.1]oct-8-yl]-amine

Chemical Property of [(rac)-8-(3,4-difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[(rac)-8-endo-3-(3-methyl-[1,2,4]thiadiazol-5-yl)-3-aza-bicyclo[3.2.1]oct-8-yl]-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(rac)-8-(3,4-difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[(rac)-8-endo-3-(3-methyl-[1,2,4]thiadiazol-5-yl)-3-aza-bicyclo[3.2.1]oct-8-yl]-amine

There total 8 articles about [(rac)-8-(3,4-difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[(rac)-8-endo-3-(3-methyl-[1,2,4]thiadiazol-5-yl)-3-aza-bicyclo[3.2.1]oct-8-yl]-amine 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: 57.0%

5-chloro-3-methyl-1,2,4-thiazole (21734-85-0) + N-((rac)-8-endo-3-azabicyclo[3.2.1]octan-8-yl)-(rac)-(3,4-difluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride → [(rac)-8-(3,4-difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[(rac)-8-endo-3-(3-methyl-[1,2,4]thiadiazol-5-yl)-3-aza-bicyclo[3.2.1]oct-8-yl]-amine (1397287-23-8)

Guidance literature:

With triethylamine; In ethanol; at 100 ℃;

Reference yield:

(rac)-3-benzyl-3-azabicyclo[3.2.1]octan-8-one oxime → [(rac)-8-(3,4-difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[(rac)-8-endo-3-(3-methyl-[1,2,4]thiadiazol-5-yl)-3-aza-bicyclo[3.2.1]oct-8-yl]-amine (1397287-23-8)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen / Raney nickel / methanol / 1 h

2: sodium phenoxide / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 0.5 h / 130 °C / Inert atmosphere; Sealed tube

3: hydrogen / hydrogenchloride; palladium 10% on activated carbon / ethanol; water / 24 h / 50 °C / 37503.8 Torr

4: triethylamine / ethanol / 100 °C

With hydrogen; sodium phenoxide; triethylamine; hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium 10% on activated carbon; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; methanol; ethanol; water;

Reference yield:

2-Amino-3-bromopyridine (13534-99-1) → [(rac)-8-(3,4-difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[(rac)-8-endo-3-(3-methyl-[1,2,4]thiadiazol-5-yl)-3-aza-bicyclo[3.2.1]oct-8-yl]-amine (1397287-23-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1,4-dioxane / 5 h / 20 °C

2: N-ethyl-N,N-diisopropylamine; hydroxylamine / ethanol; methanol / 4 h / 20 - 60 °C

3: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 18 h / 110 °C

4: tert.-butylnitrite / acetonitrile / 2 h / 60 - 75 °C

5: sodium phenoxide / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.5 h / 130 °C / Inert atmosphere; Sealed tube

6: hydrogen / hydrogenchloride; palladium 10% on activated carbon / ethanol; water / 24 h / 50 °C / 37503.8 Torr

7: triethylamine / ethanol / 100 °C

With tert.-butylnitrite; hydrogen; hydroxylamine; sodium phenoxide; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; methanol; ethanol; water; acetonitrile; 3: Suzuki Coupling;

upstream raw materials:

2-Amino-3-bromopyridine

5-chloro-3-methyl-1,2,4-thiazole

N-(3-bromo-2-pyridinyl)-N’-carboethoxy-thiourea

8-bromo-[1,2,4]triazolo[1,5-a]pyridine-2-ylamine