tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate
• CAS No.: 1038916-11-8
• Molecular Formula: C24H28N4O3
• Molecular Weight: 420.511
• Mol file: 1038916-11-8.mol

Synonyms:tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate

Chemical Property of tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate

Chemical Property:

• PSA: 90.45000
• LogP: 4.87710

Purity/Quality:

99% ^*data from raw suppliers

98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate

There total 23 articles about tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate 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: 72.0%

2-[4-((3S)-(tertbutoxycarbonyl)piperidin-3-yl)phenyl]-2H-indazole-7-carboxylic acid methyl ester (1196713-67-3) → tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate (1038916-11-8)

Guidance literature:

With ammonia; In methanol; at 60 ℃; for 48h;

DOI:10.1021/jm901188v

Reference yield:

2-{4-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]phenyl}-2H-indazole-7-carboxylic acid (1038916-08-3) → tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate (1038916-11-8)

Guidance literature:

2-{4-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]phenyl}-2H-indazole-7-carboxylic acid; With pyridine; di-tert-butyl dicarbonate; In dichloromethane; at 20 ℃; for 0.5h;

With ammonium bicarbonate; In dichloromethane; for 20h;

Reference yield:

tert-butyl (E)-3-(4-((3-carbamoyl-2-nitrobenzylidene)amino)phenyl)piperidine-1-carboxylate → tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate (1038916-11-8)

Guidance literature:

With 2,6-dimethylpyridine; sodium azide; In N,N-dimethyl-formamide; at 120 ℃; for 8h; Temperature; Reagent/catalyst; Inert atmosphere;

upstream raw materials:

2-{4-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]phenyl}-2H-indazole-7-carboxylic acid

2-[4-((3S)-(tertbutoxycarbonyl)piperidin-3-yl)phenyl]-2H-indazole-7-carboxylic acid methyl ester

(3S)-3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester

3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

2-[4-((3S)-3-piperidinyl)phenyl]-2H-indazole-7-carboxamide p-toluenesulfonic acid salt

(3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidinium fumarate

(3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidinium sulfate

(3S)-3-[4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl]piperidinium chloride

Refernces

• 1、 Wallace, Debra J.,Baxter, Carl A.,Brands, Karel J. M.,Bremeyer, Nadine,Brewer, Sarah E.,Desmond, Richard,Emerson, Khateeta M.,Foley, Jennifer,Fernandez, Paul,Hu, Weifeng,Keen, Stephen P.,Mullens, Peter,Muzzio, Daniel,Sajonz, Peter,Tan, Lushi,Wilson, Robert D.,Zhou, George,Zhou, Guoyue. "Development of a fit-for-purpose large-scale synthesis of an oral PARP inhibitor". . p. 831 - 840. Retrieved 2012/07/03.
• 2、 Jones, Philip,Altamura, Sergio,Boueres, Julia,Ferrigno, Federica,Fonsi, Massimiliano,Giomini, Claudia,Lamartina, Stefania,Monteagudo, Edith,Ontoria, Jesus M.,Orsale, Maria Vittoria,Palumbi, Maria Cecilia,Pesci, Silvia,Roscilli, Giuseppe,Scarpelli, Rita,Schultz-Fademrecht, Carsten,Toniatti, Carlo,Rowley, Michael. "Discovery of 2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (MK-4827): A novel oral poly(ADP-ribose)polymerase (PARP) inhibitor efficacious in BRCA-1 and -2 mutant tumors". experimental part. p. 7170 - 7185. Retrieved 2010/07/04.