N-((Hexahydro-1H-pyrrolizin-1-yl)methyl)-6-chloroimidazo(1,2-a)pyridine-8-carboxamide hydrochloride

Base Information

• Chemical Name: N-((Hexahydro-1H-pyrrolizin-1-yl)methyl)-6-chloroimidazo(1,2-a)pyridine-8-carboxamide hydrochloride
• CAS No.: 151898-33-8
• Molecular Formula: C₁₆H₁₉ClN₄O
• Molecular Weight: 318.806
• DSSTox Substance ID: DTXSID60164899
• Nikkaji Number: J557.586I
• Wikidata: Q83033984
• ChEMBL ID: CHEMBL202434
• Mol file: 151898-33-8.mol

Synonyms:N-((hexahydro-1H-pyrrolizin-1-yl)methyl)-6-chloroimidazo(1,2-a)pyridine-8-carboxamide hydrochloride;SC 53606;SC-53606

Chemical Property of N-((Hexahydro-1H-pyrrolizin-1-yl)methyl)-6-chloroimidazo(1,2-a)pyridine-8-carboxamide hydrochloride

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 53.13000
• Density: 1.49g/cm³
• LogP: 2.71450
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 318.1247389
• Heavy Atom Count: 22
• Complexity: 434

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(CCN2C1)CNC(=O)C3=CC(=CN4C3=NC=C4)Cl
• Isomeric SMILES: C1C[C@H]2[C@@H](CCN2C1)CNC(=O)C3=CC(=CN4C3=NC=C4)Cl

Technology Process of N-((Hexahydro-1H-pyrrolizin-1-yl)methyl)-6-chloroimidazo(1,2-a)pyridine-8-carboxamide hydrochloride

There total 11 articles about N-((Hexahydro-1H-pyrrolizin-1-yl)methyl)-6-chloroimidazo(1,2-a)pyridine-8-carboxamide hydrochloride 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: 82.0%

2-chloroethanal (107-20-0) + C14H19ClN4O → SC 53606 (151898-33-8)

Guidance literature:

In ethanol; at 80 ℃; for 12h; Inert atmosphere; Sealed tube;

Reference yield:

methyl 6-chloroimidazol[1,2-a]pyridine-8-carboxylate (760144-55-6) → SC 53606 (151898-33-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 75.5 percent / aq. HCl / 2 h / Heating

2: dimethylformamide / 1 h

3: 1.42 g / Et₃N / dimethylformamide / 1 h

With hydrogenchloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jm0509501

Reference yield:

2-[(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-1H-isoindole-1,3(2H)-dione (141119-76-8) → SC 53606 (151898-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine hydrate / ethanol / 15 h / 20 °C

2: 1.42 g / Et₃N / dimethylformamide / 1 h

With hydrazine hydrate; triethylamine; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm0509501

upstream raw materials:

(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethylamine

methyl 6-chloroimidazol[1,2-a]pyridine-8-carboxylate

2-[(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-1H-isoindole-1,3(2H)-dione

2-aminopyridin-3-carboxylic acid

Refernces

• 1、 Becker, Daniel P.,Flynn, Daniel L.,Moormann, Alan E.,Nosal, Roger,Villamil, Clara I.,Loeffler, Richard,Gullikson, Gary W.,Moummi, Chafiq,Yang, Dai-C.. "Pyrrolizidine esters and amides as 5-HT4 receptor agonists and antagonists". . p. 1125 - 1139. Retrieved 2007/10/03.