N-(8-Methyl-8-azabicyclo(3.2.1)oct-3-yl)-4-hydroxy-3-quinolinecarboxamide

Base Information

• Chemical Name: N-(8-Methyl-8-azabicyclo(3.2.1)oct-3-yl)-4-hydroxy-3-quinolinecarboxamide
• CAS No.: 145970-12-3
• Molecular Formula: C₁₈H₂₁N₃O₂
• Molecular Weight: 311.384
• DSSTox Substance ID: DTXSID60932737
• ChEMBL ID: CHEMBL109955
• Mol file: 145970-12-3.mol

Synonyms:endo-MAOHQC;N-(8-methyl-8-azabicyclo(3.2.1)oct-3-yl)-4-hydroxy-3-quinolinecarboxamide

Chemical Property of N-(8-Methyl-8-azabicyclo(3.2.1)oct-3-yl)-4-hydroxy-3-quinolinecarboxamide

Chemical Property:

• Vapor Pressure: 9.3E-11mmHg at 25°C
• Boiling Point: 516.1°C at 760 mmHg
• Flash Point: 265.9°C
• PSA: 68.69000
• Density: 1.29g/cm³
• LogP: 2.39580
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 311.16337692
• Heavy Atom Count: 23
• Complexity: 530

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCC1CC(C2)NC(=O)C3=CNC4=CC=CC=C4C3=O

Technology Process of N-(8-Methyl-8-azabicyclo(3.2.1)oct-3-yl)-4-hydroxy-3-quinolinecarboxamide

There total 4 articles about N-(8-Methyl-8-azabicyclo(3.2.1)oct-3-yl)-4-hydroxy-3-quinolinecarboxamide 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: 100.0%

4-Chloro-quinoline-3-carboxylic acid ((1S,3S,5R)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide → exo-N-(8-methyl-8-azabicyclo<3.2.1>oct-3-yl)-4-hydroxy-3-quinolinecarboxamide (145970-12-3)

Guidance literature:

With hydrogenchloride; at 80 ℃; for 13h;

DOI:10.1021/jm00057a011

Reference yield: 100.0%

endo-N-(8-methyl-8-azabicyclo<3.2.1>oct-3-yl)-4-chloro-3-quinolinecarboxamide (145970-08-7) → endo-N-(8-methyl-8-azabicyclo<3.2.1>oct-3-yl)-4-hydroxy-3-quinolinecarboxamide (145970-12-3)

Guidance literature:

With hydrogenchloride; at 80 ℃; for 13h;

DOI:10.1021/jm00057a011

Reference yield:

4-hydroxy-3-quinoline carboxylic acid (34785-11-0) → endo-N-(8-methyl-8-azabicyclo<3.2.1>oct-3-yl)-4-hydroxy-3-quinolinecarboxamide (145970-12-3)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂, DMF / 2 h / Ambient temperature

2: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, RT, 2 h

3: 100 percent / 1 N HCl / 13 h / 80 °C

With hydrogenchloride; thionyl chloride; sodium hydride; N,N-dimethyl-formamide;

DOI:10.1021/jm00057a011

upstream raw materials:

endo-N-(8-methyl-8-azabicyclo<3.2.1>oct-3-yl)-4-chloro-3-quinolinecarboxamide

4-hydroxy-3-quinoline carboxylic acid

4-chloroquinoline-3-carbonyl chloride