5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)-ethyl]-amide

Base Information

• Chemical Name: 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)-ethyl]-amide
• CAS No.: 868273-06-7
• Molecular Formula: C₂₄H₂₈ClN₃O
• Molecular Weight: 409.959
• Hs Code.: 2933990090
• Mol file: 868273-06-7.mol

Synonyms:Org 27569;

Chemical Property of 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)-ethyl]-amide

Chemical Property:

• Vapor Pressure: 2.61E-17mmHg at 25°C
• Refractive Index: 1.635
• Boiling Point: 660.3 ºC at 760 mmHg
• PKA: 14.87±0.30(Predicted)
• Flash Point: 353.2 ºC
• PSA: 48.13000
• Density: 1.218
• LogP: 5.80240
• Storage Temp.: 2-8°C
• Solubility.: H2O:

Purity/Quality:

99%+, ^*data from raw suppliers

Org 27569 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Org 27569 is a drug that is a used in biological studies for structure-activity relationships of indole-carboxamides as CB1 receptor allosteric modulators.

Technology Process of 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)-ethyl]-amide

There total 14 articles about 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)-ethyl]-amide 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: 77.0%

2-[4-(piperidin-1-yl)phenyl]ethan-1-amine (38589-09-2) + 5-chloro-3-ethyl-1H-indole-2-carboxylic acid (446830-67-7) → Org 27569 (868273-06-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b01303

Reference yield:

ethyl 5-chloro-3-ethyl-1H-indole-2-carboxylate (1377838-23-7) → Org 27569 (868273-06-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / ethanol / 60 °C

1.2: pH 2

2.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; sodium hydroxide; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm201485c

Reference yield:

2-(4-(piperidin-1-yl)phenethyl)isoindoline-1,3-dione (1377838-25-9) → Org 27569 (868273-06-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine hydrate / ethanol / Reflux

2: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; hydrazine hydrate; triethylamine; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm201485c

upstream raw materials:

2-[4-(piperidin-1-yl)phenyl]ethan-1-amine

5-chloro-3-ethyl-1H-indole-2-carboxylic acid

ethyl 3-acetyl-5-chloro-1H-indole-2-carboxylate

2-(4-(piperidin-1-yl)phenethyl)isoindoline-1,3-dione

Refernces

• 1、 Piscitelli, Francesco,Ligresti, Alessia,La Regina, Giuseppe,Coluccia, Antonio,Morera, Ludovica,Allarà, Marco,Novellino, Ettore,Di Marzo, Vincenzo,Silvestri, Romano. "Indole-2-carboxamides as allosteric modulators of the cannabinoid CB 1 receptor". supporting information; experimental part. p. 5627 - 5631. Retrieved 2012/08/28.