(S,E)-4-(8-amino-3-(1-(4-(pyrrolidin-1-yl)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide

Base Information

• Chemical Name: (S,E)-4-(8-amino-3-(1-(4-(pyrrolidin-1-yl)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide
• CAS No.: 1420477-56-0
• Molecular Formula: C₃₀H₃₂N₈O₂
• Molecular Weight: 536.636
• Mol file: 1420477-56-0.mol

Synonyms:(S,E)-4-(8-amino-3-(1-(4-(pyrrolidin-1-yl)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide

Chemical Property of (S,E)-4-(8-amino-3-(1-(4-(pyrrolidin-1-yl)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-4-(8-amino-3-(1-(4-(pyrrolidin-1-yl)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide

There total 6 articles about (S,E)-4-(8-amino-3-(1-(4-(pyrrolidin-1-yl)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide 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: 26.8%

4-{8-amino-3-[(2S)-pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl}-N-(pyridin-2-yl)benzamide (1420478-90-5) + (E)-4-(pyrrolidin-1-yl)but-2-enoic acid hydrochloride (848133-09-5) → (S,E)-4-(8-amino-3-(1-(4-(pyrrolidin-1-yl)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide (1420477-56-0)

Guidance literature:

With triethylamine; HATU; In dichloromethane; at 20 ℃; for 0.5h;

Reference yield:

(S)-2-(8-chloroimidazo[1,5-a]pyrazin-3-yl)-1-pyrrolidinecarboxylic acid benzyl ester (1418307-18-2) → (S,E)-4-(8-amino-3-(1-(4-(pyrrolidin-1-yl)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide (1420477-56-0)

Guidance literature:

Multi-step reaction with 5 steps

1: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 20 °C

2: ammonia / isopropyl alcohol / -78 - 110 °C / 3000.3 - 3375.34 Torr

3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.33 h / 140 °C / Inert atmosphere; Microwave irradiation

4: hydrogen bromide / acetic acid / 1 h / 20 °C

5: triethylamine; HATU / dichloromethane / 0.5 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; ammonia; hydrogen bromide; potassium carbonate; triethylamine; HATU; In 1,4-dioxane; dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

benzyl (2S)-2-(1-bromo-8-chloro-imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (1420478-87-0) → (S,E)-4-(8-amino-3-(1-(4-(pyrrolidin-1-yl)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide (1420477-56-0)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonia / isopropyl alcohol / -78 - 110 °C / 3000.3 - 3375.34 Torr

2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.33 h / 140 °C / Inert atmosphere; Microwave irradiation

3: hydrogen bromide / acetic acid / 1 h / 20 °C

4: triethylamine; HATU / dichloromethane / 0.5 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonia; hydrogen bromide; potassium carbonate; triethylamine; HATU; In 1,4-dioxane; dichloromethane; acetic acid; isopropyl alcohol;

upstream raw materials:

(S)-2-(8-chloroimidazo[1,5-a]pyrazin-3-yl)-1-pyrrolidinecarboxylic acid benzyl ester

benzyl (2S)-2-(1-bromo-8-chloro-imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate

benzyl (2S)-2-(8-amino-1-bromo-imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate

4-{8-amino-3-[(2S)-pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl}-N-(pyridin-2-yl)benzamide