(3R)-3-[4-(Butylthio)-1,2,5-thiadiazol-3-yl]-1-azabicyclo[2.2.2]octane

Base Information

• Chemical Name: (3R)-3-[4-(Butylthio)-1,2,5-thiadiazol-3-yl]-1-azabicyclo[2.2.2]octane
• CAS No.: 141575-52-2
• Molecular Formula: C₁₃H₂₁N₃S₂
• Molecular Weight: 283.462
• DSSTox Substance ID: DTXSID101015356
• Wikidata: Q101428108
• Mol file: 141575-52-2.mol

Synonyms:DTXSID101015356;141575-52-2;(3R)-3-[4-(Butylthio)-1,2,5-thiadiazol-3-yl]-1-azabicyclo[2.2.2]octane

Chemical Property of (3R)-3-[4-(Butylthio)-1,2,5-thiadiazol-3-yl]-1-azabicyclo[2.2.2]octane

Chemical Property:

• Vapor Pressure: 6.7E-06mmHg at 25°C
• Boiling Point: 377.5°C at 760 mmHg
• Flash Point: 182.1°C
• Density: 1.23g/cm³
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 283.11769003
• Heavy Atom Count: 18
• Complexity: 269

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCSC1=NSN=C1C2CN3CCC2CC3
• Isomeric SMILES: CCCCSC1=NSN=C1[C@H]2CN3CCC2CC3

Technology Process of (3R)-3-[4-(Butylthio)-1,2,5-thiadiazol-3-yl]-1-azabicyclo[2.2.2]octane

There total 19 articles about (3R)-3-[4-(Butylthio)-1,2,5-thiadiazol-3-yl]-1-azabicyclo[2.2.2]octane 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:

3-quinuclidinone hydrochloride (1193-65-3) → 3-[4-(butylthio)-1,2,5-thiadiazol-3-yl]-1-azabicyclo-[2.2.2]octane (141593-42-2,141575-52-2)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / 2 h / 80 °C

2: H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

3: 1.) NaOMe, NaOEt, 2.) isoamyl nitrite, 3.) S₂Cl₂

4: H₂ / 5percentPd/C / ethanol / 760 Torr / Ambient temperature

5: NaHS*H₂O, K₂CO₃ / dimethylformamide / 2 h / Ambient temperature

6: dimethylformamide

With disulfur dichloride; sodium hydrogensulfide; hydrogen; sodium methylate; sodium ethanolate; potassium carbonate; triethylamine; isopentyl nitrite; palladium on activated charcoal; 5% Pd on active carbon; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm9602470

Reference yield:

3-quinuclidinone hydrochloride (1193-65-3) → LY297802/NNC11-1053 (141575-52-2)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N / 2 h / 80 °C

2: H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

3: 1.) NaOMe, NaOEt, 2.) isoamyl nitrite, 3.) S₂Cl₂

4: H₂ / 5percentPd/C / ethanol / 760 Torr / Ambient temperature

5: NaHS*H₂O, K₂CO₃ / dimethylformamide / 2 h / Ambient temperature

6: dimethylformamide

With disulfur dichloride; sodium hydrogensulfide; hydrogen; sodium methylate; sodium ethanolate; potassium carbonate; triethylamine; isopentyl nitrite; palladium on activated charcoal; 5% Pd on active carbon; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm9602470

Reference yield:

ethyl(1-azabicyclo[2.2.2]octan-3-ylidene)cyanoacetate (141593-49-9) → 3-[4-(butylthio)-1,2,5-thiadiazol-3-yl]-1-azabicyclo-[2.2.2]octane (141593-42-2,141575-52-2)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

2: 1.) NaOMe, NaOEt, 2.) isoamyl nitrite, 3.) S₂Cl₂

3: H₂ / 5percentPd/C / ethanol / 760 Torr / Ambient temperature

4: NaHS*H₂O, K₂CO₃ / dimethylformamide / 2 h / Ambient temperature

5: dimethylformamide

With disulfur dichloride; sodium hydrogensulfide; hydrogen; sodium methylate; sodium ethanolate; potassium carbonate; isopentyl nitrite; palladium on activated charcoal; 5% Pd on active carbon; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm9602470

upstream raw materials:

1-bromo-butane

3-(3-CHLORO-1,2,5-THIADIAZOL-4-YL)-1-AZABICYCLO[2.2.2]OCTANE

3-quinuclidinone hydrochloride

ethyl(1-azabicyclo[2.2.2]octan-3-ylidene)cyanoacetate

Refernces

• 1、 -. "Method of treating hypercholesterolemia and related disorders". . . Retrieved 2008/06/13.
• 2、 -. "METHOD FOR TREATING ANXIETY". . . Retrieved 2008/06/13.