3-(1-(3-cyanophenyl)-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide

Base Information

• Chemical Name: 3-(1-(3-cyanophenyl)-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide
• CAS No.: 1025482-21-6
• Molecular Formula: C₂₈H₂₃N₅OS
• Molecular Weight: 477.59
• Mol file: 1025482-21-6.mol

Synonyms:

Chemical Property of 3-(1-(3-cyanophenyl)-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(1-(3-cyanophenyl)-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide

There total 10 articles about 3-(1-(3-cyanophenyl)-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide 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:

3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid (1025482-61-4) → 3-(1-(3-cyanophenyl)-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide (1025482-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate / N,N-dimethyl-formamide / 90 °C

2: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; 1: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2013.08.049

Reference yield:

6-chloronicotinylaldehyde (23100-12-1) → 3-(1-(3-cyanophenyl)-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide (1025482-21-6)

Guidance literature:

Multi-step reaction with 11 steps

1: phenylmagnesium bromide / tetrahydrofuran

2: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane

3: titanium tetrachloride / dichloromethane

4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; zinc / N,N-dimethyl acetamide / 2 h / 120 °C

5: hydrogen; palladium on activated charcoal; hydrogenchloride / methanol / 2.5 h

6: 90 °C

7: trichlorophosphate / toluene / 115 °C

8: N-Bromosuccinimide / acetonitrile / -10 - 20 °C

9: lithium hydroxide / water; 1,4-dioxane

10: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate / N,N-dimethyl-formamide / 90 °C

11: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

With hydrogenchloride; dmap; potassium phosphate; N-Bromosuccinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium on activated charcoal; hydrogen; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; phenylmagnesium bromide; HATU; lithium hydroxide; zinc; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; toluene; acetonitrile; 10: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2013.08.049

Reference yield:

6-chloro-α-phenyl-3-pyridinemethanol (80100-47-6) → 3-(1-(3-cyanophenyl)-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide (1025482-21-6)

Guidance literature:

Multi-step reaction with 10 steps

1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane

2: titanium tetrachloride / dichloromethane

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; zinc / N,N-dimethyl acetamide / 2 h / 120 °C

4: hydrogen; palladium on activated charcoal; hydrogenchloride / methanol / 2.5 h

5: 90 °C

6: trichlorophosphate / toluene / 115 °C

7: N-Bromosuccinimide / acetonitrile / -10 - 20 °C

8: lithium hydroxide / water; 1,4-dioxane

9: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate / N,N-dimethyl-formamide / 90 °C

10: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

With hydrogenchloride; dmap; potassium phosphate; N-Bromosuccinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium on activated charcoal; hydrogen; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; HATU; lithium hydroxide; zinc; trichlorophosphate; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; toluene; acetonitrile; 9: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2013.08.049

upstream raw materials:

3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid

2-thiazolylamine

3-(1-(3-cyanophenyl)-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid

6-chloronicotinylaldehyde