4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester
• CAS No.: 756870-01-6
• Molecular Formula: C₂₇H₃₇N₅O₃S
• Molecular Weight: 511.688
• Mol file: 756870-01-6.mol

Synonyms:

Chemical Property of 4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

There total 3 articles about 4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester 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:

4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenylboronic acid (457613-78-4) + (S)-2-(4-Bromo-thiophen-3-ylamino)-4-methyl-pentanoic acid cyanomethyl-amide (459164-84-2) → 4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (756870-01-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In N,N-dimethyl-formamide; at 85 - 90 ℃;

DOI:10.1016/j.bmcl.2004.05.087

Reference yield:

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) → 4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (756870-01-6)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃; CuI / dimethylformamide / Heating

2: PyBOP; Et₃N / dimethylformamide

3: aq. Na₂CO₃; PdCl₂(dppf) / dimethylformamide / 85 - 90 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium carbonate; potassium carbonate; triethylamine; In N,N-dimethyl-formamide; 3: Suzuki cross-coupling;

DOI:10.1016/j.bmcl.2004.05.087

Reference yield:

(S)-2-(4-Bromo-thiophen-3-ylamino)-4-methyl-pentanoic acid (756870-00-5) → 4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (756870-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1: PyBOP; Et₃N / dimethylformamide

2: aq. Na₂CO₃; PdCl₂(dppf) / dimethylformamide / 85 - 90 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium carbonate; triethylamine; In N,N-dimethyl-formamide; 2: Suzuki cross-coupling;

DOI:10.1016/j.bmcl.2004.05.087

upstream raw materials:

4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenylboronic acid

(S)-2-(4-Bromo-thiophen-3-ylamino)-4-methyl-pentanoic acid cyanomethyl-amide

L-leucine

(S)-2-(4-Bromo-thiophen-3-ylamino)-4-methyl-pentanoic acid