1-[3,5-Bis(trifluoromethyl)phenyl)-3-{(S)[(2S,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-4-quinolinyl)methyl}thiourea

Base Information

• Chemical Name: 1-[3,5-Bis(trifluoromethyl)phenyl)-3-{(S)[(2S,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-4-quinolinyl)methyl}thiourea
• CAS No.: 852913-19-0
• Molecular Formula: C₂₉H₃₀F₆N₄OS
• Molecular Weight: 596.64
• Hs Code.: 2939200000
• European Community (EC) Number: 635-377-6
• DSSTox Substance ID: DTXSID20457471
• Nikkaji Number: J3.079.249A,J2.178.287D
• ChEMBL ID: CHEMBL5170136
• Mol file: 852913-19-0.mol

Synonyms:852913-19-0;1-(3,5-Bis(trifluoromethyl)phenyl)-3-((S)-((1S,2S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea;1-[3,5-Bis(trifluoromethyl)phenyl)-3-{(S)[(2S,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-4-quinolinyl)methyl}thiourea;1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(S)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]thiourea;N-[35-Bis(trifluoromethyl)phenyl]-N'-[(8alpha9S)-1011-dihydro-6'-methoxycinchonan-9-yl]thiourea;1-(3,5-Bis(trifluoromethyl)phenyl)-3-((1S)-((8R)-8-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea;CHEMBL5170136;SCHEMBL14128330;SCHEMBL16858672;DTXSID20457471;MFCD16875669;CS-0091869;D75246;(8S,9S)-6'-Methoxy-9-[3-[3,5-bis(trifluoromethyl)phenyl]thioureido]-10,11-dihydrocinchonan;1-(3,5-Bis(trifluoromethyl)phenyl)-3-((1S)-((2S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea;1-[(S)-[(2S,4S,5R)-5-Ethylquinuclidine-2-yl](6-methoxy-4-quinolinyl)methyl]-3-[3,5-bis(trifluoromethyl)phenyl]thiourea;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8,9S)-10,11-dihydro-6'-methoxycinchonan-9-yl]thiourea;N-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-N'-[(8| inverted exclamation mark,9S)-10,11-DIHYDRO-6'-METHOXYCINCHONAN-9-YL]THIOUREA;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8|A,9S)-10,11-dihydro-6'-methoxycinchonan-9-yl]thiourea;N-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-N'-[(8A,9S)-10,11-DIHYDRO-6'-METHOXY-9-CINCHONANYL]THIOUREA;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8a,9S)-10,11-dihydro-6'-methoxy-9-cinchonanyl]thiourea, 90%

Chemical Property of 1-[3,5-Bis(trifluoromethyl)phenyl)-3-{(S)[(2S,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-4-quinolinyl)methyl}thiourea

Chemical Property:

• Boiling Point: 600.8±65.0 °C(Predicted)
• PKA: 11.39±0.70(Predicted)
• PSA: 81.51000
• Density: 1.38±0.1 g/cm3(Predicted)
• LogP: 7.83090
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 596.20445174
• Heavy Atom Count: 41
• Complexity: 884

Purity/Quality:

97% ^*data from raw suppliers

N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(8a,9S)-10,11-dihydro-6′-methoxy-9-cinchonanyl]thiourea 90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)NC(=S)NC5=CC(=CC(=C5)C(F)(F)F)C(F)(F)F
• Isomeric SMILES: CC[C@H]1CN2CC[C@H]1C[C@H]2[C@H](C3=C4C=C(C=CC4=NC=C3)OC)NC(=S)NC5=CC(=CC(=C5)C(F)(F)F)C(F)(F)F

Technology Process of 1-[3,5-Bis(trifluoromethyl)phenyl)-3-{(S)[(2S,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-4-quinolinyl)methyl}thiourea

There total 6 articles about 1-[3,5-Bis(trifluoromethyl)phenyl)-3-{(S)[(2S,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-4-quinolinyl)methyl}thiourea 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: 81.0%

9-amino-9-deoxy-epihydroquinine (852913-53-2) + 3,5-bistrifluoromethylphenylisothiocyanate (23165-29-9) → 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((2S,4S,8R)-8-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea (852913-19-0)

Guidance literature:

In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol050431s

Reference yield: 10.0%

(R)-((1S,2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methanamine (522600-31-3) + 3,5-bistrifluoromethylphenylisothiocyanate (23165-29-9) → 1-(3,5-Bis-trifluoromethyl-phenyl)-3-[(R)-((1S,2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl]-thiourea (852913-19-0)

Guidance literature:

In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/anie.200501721

Reference yield:

4-[(R)-Azido-((1S,2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-6-methoxy-quinoline → 1-(3,5-Bis-trifluoromethyl-phenyl)-3-[(R)-((1S,2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl]-thiourea (852913-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphane / tetrahydrofuran / 4 h / 45 °C

2: 10 percent / CH₂Cl₂ / 0 - 20 °C

With triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.200501721

upstream raw materials:

9-amino-9-deoxy-epihydroquinine

3,5-bistrifluoromethylphenylisothiocyanate

dihydroquinine

(R)-((1S,2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methanamine