(S)-[(2S,4S,5R)-5-Ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanamine

Base Information

• Chemical Name: (S)-[(2S,4S,5R)-5-Ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanamine
• CAS No.: 852913-53-2
• Molecular Formula: C20H25N3O
• Molecular Weight: 325.454
• European Community (EC) Number: 814-332-6
• ChEMBL ID: CHEMBL5181171
• Nikkaji Number: J2.434.782F
• Mol file: 852913-53-2.mol

Synonyms:(S)-[(2S,4S,5R)-5-Ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanamine;852913-53-2;CHEMBL5181171;SCHEMBL25209392;(8|A,9S)-9-Amine-10,11-dihydro-6'-methoxy-Cinchonan

Chemical Property of (S)-[(2S,4S,5R)-5-Ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanamine

Chemical Property:

• Boiling Point: 487.5±30.0 °C(Predicted)
• PKA: 9.98±0.70(Predicted)
• PSA: 51.38000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 3.77780
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 325.215412493
• Heavy Atom Count: 24
• Complexity: 431

Purity/Quality:

97% ^*data from raw suppliers

(8α, 9S)-10,11-Dihydro-6'-methoxycinchonan-9-amine trihydrochloride, min. 90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)N
• Isomeric SMILES: CC[C@H]1CN2CC[C@H]1C[C@H]2[C@H](C3=C4C=C(C=CC4=NC=C3)OC)N

Technology Process of (S)-[(2S,4S,5R)-5-Ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanamine

There total 14 articles about (S)-[(2S,4S,5R)-5-Ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanamine 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: 95.0%

9-epi-9-amino-9-deoxyquinine → 9-amino-9-deoxy-epihydroquinine (852913-53-2)

Guidance literature:

With palladium on activated charcoal; In methanol; for 3h; under 2280.15 Torr;

DOI:10.1039/c4ob01472c

Reference yield: 93.0%

(S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanamine hydrochloride (1231763-32-8,18797-90-5) → 9-amino-9-deoxy-epihydroquinine (852913-53-2)

Guidance literature:

9-deoxy-9-epi-aminoquinine trishydrochloride; With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In methanol; water; at 20 ℃; for 15h; under 760.051 Torr;

With ammonium hydroxide; In dichloromethane; water; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201804099

Reference yield: 76.0%

dihydroquinine (522-66-7) → (1S)-[((2S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)]methanamine (852913-53-2)

Guidance literature:

dihydroquinine; With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; In dichloromethane; at 0 - 25 ℃;

In dichloromethane; water; at 25 ℃;

DOI:10.3390/molecules26216542

upstream raw materials:

dihydroquinine

quinine

quinine 9O-methanesulfonate

(8S,9S)-9-azido-(9-deoxy)epiquinine

Downstream raw materials:

1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((2S,4S,8R)-8-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea

1-(2,6-diisopropylphenyl)-3-((1S)-((2S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea

3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((1S)-((2S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)amino)cyclobut-3-ene-1,2-dione

2-(diphenylphosphino)-N-((S)-((1S,2S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)benzamide