4-(4-{4-[1-(cyanomethylcarbamoyl)cyclohexylcarbamoyl]phenyl}thiazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-(4-{4-[1-(cyanomethylcarbamoyl)cyclohexylcarbamoyl]phenyl}thiazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 871828-55-6
• Molecular Formula: C₂₉H₃₇N₅O₄S
• Molecular Weight: 551.71
• Mol file: 871828-55-6.mol

Synonyms:4-(4-{4-[1-(cyanomethylcarbamoyl)cyclohexylcarbamoyl]phenyl}thiazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of 4-(4-{4-[1-(cyanomethylcarbamoyl)cyclohexylcarbamoyl]phenyl}thiazol-2-yl)piperidine-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-(cyanomethylcarbamoyl)cyclohexylcarbamoyl]phenyl}thiazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester

There total 6 articles about 4-(4-{4-[1-(cyanomethylcarbamoyl)cyclohexylcarbamoyl]phenyl}thiazol-2-yl)piperidine-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: 39.0%

4-[4-(4-carboxy-phenyl)-thiazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester + 1-amino-N-(cyanomethyl)cyclohexanecarboxamide methanesulfonate → 4-(4-{4-[1-(cyanomethylcarbamoyl)cyclohexylcarbamoyl]phenyl}thiazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester (871828-55-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/jm058198r

Reference yield:

tert-butyl 4-carbamothioylpiperidine-1-carboxylate (214834-18-1) → 4-(4-{4-[1-(cyanomethylcarbamoyl)cyclohexylcarbamoyl]phenyl}thiazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester (871828-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.55 g / tetrahydrofuran / 3 h / 70 °C

2: 39 percent / HATU; diisopropylethylamine / dimethylformamide / 3 h / 20 °C

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm058198r

Reference yield:

4-acetyl-benzoic acid (586-89-0) → 4-(4-{4-[1-(cyanomethylcarbamoyl)cyclohexylcarbamoyl]phenyl}thiazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester (871828-55-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / Br₂; AcOH / 1 h / 80 °C

2: 2.55 g / tetrahydrofuran / 3 h / 70 °C

3: 39 percent / HATU; diisopropylethylamine / dimethylformamide / 3 h / 20 °C

With bromine; acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm058198r

upstream raw materials:

tert-butyl 4-carbamothioylpiperidine-1-carboxylate

4-acetyl-benzoic acid

4-(2-bromoacetyl)benzoic acid

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid