3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 4-methylbenzenesulfonate

Base Information

• Chemical Name: 3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 4-methylbenzenesulfonate
• CAS No.: 423165-08-6
• Molecular Formula: C20H30N4O3S
• Molecular Weight: 406.549
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40436980
• Mol file: 423165-08-6.mol

Synonyms:423165-08-6;3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 4-methylbenzenesulfonate;1545932-86-2;4-methylbenzenesulfonic acid;3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane;3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane4-methylbenzenesulfonate;3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-aza-bicyclo[3.2.1]octane 4-methylbenzenesulfonate;SCHEMBL3876623;DTXSID40436980;YRA16508;MFCD22422952;AKOS015918517;WS-01875;F10399;(3-exo)-3-[3-Methyl-5-(1-methylethyl-D6)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octane 4-Methylbenzenesulfonate;3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane P-toluenesulfonate

Chemical Property of 3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 4-methylbenzenesulfonate

Chemical Property:

• Vapor Pressure: 1.1E-06mmHg at 25°C
• Boiling Point: 402.4 °C at 760 mmHg
• Flash Point: 197.1 °C
• PSA: 105.49000
• LogP: 4.81670
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 406.20386201
• Heavy Atom Count: 28
• Complexity: 475

Purity/Quality:

99%, ^*data from raw suppliers

3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 4-methylbenzenesulfonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.CC1=NN=C(N1C2CC3CCC(C2)N3)C(C)C
• Use Description: 3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane-p-toluenesulfonate is a specific chemical compound with diverse applications in various fields. In the realm of pharmaceuticals and medicinal chemistry, it serves as an important ligand for specific receptors, making it valuable in drug discovery and the development of potential therapeutic agents. Its interaction with biological targets can aid in the study of neurological disorders and the development of medications that modulate the central nervous system. Moreover, in chemical research and synthesis, this compound can be employed as a versatile building block for the creation of complex molecules, contributing to advancements in organic chemistry. Its applications in pharmaceuticals and chemical research underscore its significance in driving innovation, scientific exploration, and potential medical breakthroughs within these distinct domains.

Technology Process of 3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 4-methylbenzenesulfonate

There total 8 articles about 3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 4-methylbenzenesulfonate 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: 92.0%

exo-8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane (423165-13-3) + toluene-4-sulfonic acid (104-15-4) → exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate (423165-08-6,1545932-86-2)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 50 ℃; under 2250.23 Torr; Solvent; Time; Inert atmosphere; Large scale;

DOI:10.1021/op800062d

Reference yield:

8-Benzyl-1αH,5αH-nortropan-3-one Oxime (76272-34-9) → exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate (423165-08-6,1545932-86-2)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium; propan-1-ol / toluene / 12 h / Reflux; Inert atmosphere

2: tetrahydrofuran / 72 h / 20 °C / Inert atmosphere

3: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere

4: sodium carbonate / water; dichloromethane / 0 - 20 °C / Inert atmosphere

5: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

6: dichloromethane; tert-Amyl alcohol / 0 - 20 °C / Inert atmosphere

7: acetic acid / ethyl acetate / 0.5 h / 80 °C / Inert atmosphere

8: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / Inert atmosphere

With hydrogenchloride; propan-1-ol; phosphorus pentachloride; palladium 10% on activated carbon; hydrogen; sodium; sodium carbonate; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; tert-Amyl alcohol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/ml400370w

Reference yield:

8-benzyl-8-azabicyclo[3.2.1]octan-3-amine → exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate (423165-08-6,1545932-86-2)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran / 72 h / 20 °C / Inert atmosphere

2: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere

3: sodium carbonate / water; dichloromethane / 0 - 20 °C / Inert atmosphere

4: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

5: dichloromethane; tert-Amyl alcohol / 0 - 20 °C / Inert atmosphere

6: acetic acid / ethyl acetate / 0.5 h / 80 °C / Inert atmosphere

7: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / Inert atmosphere

With hydrogenchloride; phosphorus pentachloride; palladium 10% on activated carbon; hydrogen; sodium carbonate; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; tert-Amyl alcohol; dichloromethane; water; ethyl acetate;

DOI:10.1021/ml400370w

upstream raw materials:

exo-8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane

toluene-4-sulfonic acid

8-Benzyl-1αH,5αH-nortropan-3-one Oxime

exo-(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-carbamic acid tert-butyl ester

Downstream raw materials:

benzyl (S)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropylcarbamate

maraviroc

N-((S)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropyl)cyclohexanecarboxamide

benzyl (S)-1-(4-chlorophenyl)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)propylcarbamate

Refernces

• 1、 Asano, Shigehiro,Gavrilyuk, Julia,Burton, Dennis R.,Barbas, Carlos F.. "Preparation and activities of macromolecule conjugates of the CCR5 antagonist maraviroc". supporting information. p. 133 - 137. Retrieved 2014/03/21.
• 2、 Ahman, Jens,Birch, Melissa,Haycock-Lewandowski, Sarah J.,Long, James,Wilder, Alexander. "Process research and scale-up of a commercialisable route to maraviroc (UK-427,857), a CCR-5 receptor antagonist". . p. 1104 - 1113. Retrieved 2013/01/03.