(S)-2-(4-(piperidin-3-yl)phenyl)-2H-indazole-7-carboxaMide

Base Information

• Chemical Name: (S)-2-(4-(piperidin-3-yl)phenyl)-2H-indazole-7-carboxaMide
• CAS No.: 1038915-64-8
• Molecular Formula: C19H20N4O
• Molecular Weight: 356.855
• Mol file: 1038915-64-8.mol

Synonyms:MK-4827 (HCl)

Chemical Property of (S)-2-(4-(piperidin-3-yl)phenyl)-2H-indazole-7-carboxaMide

Chemical Property:

• Melting Point: 144 °C
• Boiling Point: 463.619 °C at 760 mmHg
• Flash Point: 234.188 °C
• PSA: 72.94000
• Density: 1.343 g/cm³
• LogP: 4.42250

Purity/Quality:

98%,99%, ^*data from raw suppliers

Niraparib(MK4827)hydrochloride 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-(4-(piperidin-3-yl)phenyl)-2H-indazole-7-carboxaMide

There total 19 articles about (S)-2-(4-(piperidin-3-yl)phenyl)-2H-indazole-7-carboxaMide 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: 98.0%

tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate (1038916-11-8) → (3S)-3-[4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl]piperidinium chloride (1038915-64-8)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate; at 20 ℃; for 3h; optical yield given as %ee;

DOI:10.1021/jm901188v

Reference yield:

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine (1038915-60-4) → (3S)-3-[4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl]piperidinium chloride (1038915-64-8)

Guidance literature:

With hydrogenchloride; In water; for 0.25h;

DOI:10.1021/jm901188v

Reference yield:

3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester (875798-79-1) → (3S)-3-[4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl]piperidinium chloride (1038915-64-8)

Guidance literature:

Multi-step reaction with 5 steps

1: Chiralpak AD / ethanol; n-heptane / Resolution of racemate; Large scale reaction

2: tert-butyl methyl ether / 60 °C

3: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction

4: ammonia / methanol / 60 °C

5: hydrogenchloride / water; ethyl acetate / 20 °C

With hydrogenchloride; sodium azide; ammonia; In methanol; ethanol; n-heptane; tert-butyl methyl ether; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/op2000783

upstream raw materials:

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

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

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

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

Downstream raw materials:

2-(4-{(3S)-1-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]piperidin-3-yl}phenyl)-2Hindazole-7-carboxamide

2-(4-{(3S)-1-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]piperidin-3-yl}phenyl)-2Hindazole-7-carboxamide

Refernces

• 1、 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.