(R)-(5-chloro-4-(6-(2-methyl-4-pivaloylpiperazin-1-yl)nicotinamido)-2-(trifluoromethoxy)phenyl)boronic acid

Base Information

• Chemical Name: (R)-(5-chloro-4-(6-(2-methyl-4-pivaloylpiperazin-1-yl)nicotinamido)-2-(trifluoromethoxy)phenyl)boronic acid
• CAS No.: 1433280-51-3
• Molecular Formula: C₂₃H₂₇BClF₃N₄O₅
• Molecular Weight: 542.75
• Mol file: 1433280-51-3.mol

Synonyms:(R)-(5-chloro-4-(6-(2-methyl-4-pivaloylpiperazin-1-yl)nicotinamido)-2-(trifluoromethoxy)phenyl)boronic acid

Chemical Property of (R)-(5-chloro-4-(6-(2-methyl-4-pivaloylpiperazin-1-yl)nicotinamido)-2-(trifluoromethoxy)phenyl)boronic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(5-chloro-4-(6-(2-methyl-4-pivaloylpiperazin-1-yl)nicotinamido)-2-(trifluoromethoxy)phenyl)boronic acid

There total 7 articles about (R)-(5-chloro-4-(6-(2-methyl-4-pivaloylpiperazin-1-yl)nicotinamido)-2-(trifluoromethoxy)phenyl)boronic acid 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: 73.0%

Trimethyl borate (121-43-7,63156-11-6) + (R)-N-(4-bromo-2-chloro-5-(trifluoromethoxy)phenyl)-6-(2-methyl-4-pivaloylpiperazin-1-yl)nicotinamide → (R)-(5-chloro-4-(6-(2-methyl-4-pivaloylpiperazin-1-yl)nicotinamido)-2-(trifluoromethoxy)phenyl)boronic acid (1433280-51-3)

Guidance literature:

Trimethyl borate; (R)-N-(4-bromo-2-chloro-5-(trifluoromethoxy)phenyl)-6-(2-methyl-4-pivaloylpiperazin-1-yl)nicotinamide; With TurboGrignard; In tetrahydrofuran; at 0 - 20 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 0 ℃; Inert atmosphere;

Reference yield: 57.0%

Trimethyl borate (121-43-7,63156-11-6) + N-(4-bromo-2-chloro-5-trifluoromethoxy-phenyl)-6-[(R)-4-(2,2-dimethyl-propionyl)-2-methyl-piperazin-1-yl]-nicotinamide (1433280-30-8) → (R)-(5-chloro-4-(6-(2-methyl-4-pivaloylpiperazin-1-yl)nicotinamido)-2-(trifluoromethoxy)phenyl)boronic acid (1433280-51-3)

Guidance literature:

N-(4-bromo-2-chloro-5-trifluoromethoxy-phenyl)-6-[(R)-4-(2,2-dimethyl-propionyl)-2-methyl-piperazin-1-yl]-nicotinamide; With TurboGrignard; In tetrahydrofuran; at 0 - 10 ℃; for 2.5h; Inert atmosphere;

Trimethyl borate; With hydrogenchloride; In tetrahydrofuran; water;

Reference yield:

4-bromo-3-(trifluoromethoxy)phenylamine (116369-25-6) → (R)-(5-chloro-4-(6-(2-methyl-4-pivaloylpiperazin-1-yl)nicotinamido)-2-(trifluoromethoxy)phenyl)boronic acid (1433280-51-3)

Guidance literature:

Multi-step reaction with 6 steps

1: N-chloro-succinimide / acetonitrile / 60 °C

2: N,N-dimethyl acetamide / dichloromethane

3: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 120 °C

4: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 20 °C

6: TurboGrignard / tetrahydrofuran / 2.5 h / 0 - 10 °C / Inert atmosphere

With hydrogenchloride; N-chloro-succinimide; TurboGrignard; N,N-dimethyl acetamide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide; acetonitrile;

upstream raw materials:

Trimethyl borate

N-(4-bromo-2-chloro-5-trifluoromethoxy-phenyl)-6-[(R)-4-(2,2-dimethyl-propionyl)-2-methyl-piperazin-1-yl]-nicotinamide

4-bromo-3-(trifluoromethoxy)phenylamine

4-bromo-2-chloro-5-(trifluoromethoxy)phenylamine

Downstream raw materials:

(2S,4S)-2-{4-[5'-chloro-4'-({6-[(R)-4-(2,2-dimethyl-propionyl)-2-methyl-piperazin-1-yl]-pyridine-3-carbonyl}-amino)-2'-trifluoromethoxy-biphenyl-4-yl]-1H-imidazol-2-yl}-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

N-{5-chloro-4'-[2-((2S,4S)-4-methoxy-pyrrolidin-2-yl)-1H-imidazol-4-yl]-2-trifluoromethoxy-biphenyl-4-yl}-6-[(R)-4-(2,2-dimethyl-propionyl)-2-methyl-piperazin-1-yl]-nicotinamide

N-(5-chloro-4'-(2-((2S,4S)-4-methylpyrrolidin-2-yl)-1H-imidazol-4-yl)-2-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)-6-((R)-2-methyl-4-pivaloylpiperazin-1-yl)nicotinamide