423165-07-5

Basic information

• Product Name: (1R,3s,5S)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane
• Synonyms: (3-Exo)-3-[3-methyl-5-(1-methylethyl)-4H-1,2,4-triazol-4-yl] -8-Azabicyclo[3.2.1]octane;Des[1-(4,4-difluorocyclohexanecarboxamido)-1-phenylpropyl] Maraviroc;UK 408027;(1R,3s,5S)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane;8-Azabicyclo[3,2,1]octane3-[3-methyl-5-(1-methlethyl)-4H-1,2,4-triazol-4-yl]-, (3-exo)-;Maraviroc Intermediate 2;Maraviroc interMediate(Tropinone);(3-exo)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octane
• CAS NO: 423165-07-5
• Molecular Formula: C₁₃H₂₂N₄
• Molecular Weight: 234.34
• EINECS: 1533716-785-6
• Product Categories: Chiral Reagents;Metabolites & Impurities
• Mol File: 423165-07-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 117 ºC
• Boiling Point: 402.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.31
• Refractive Index: 1.678
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform
• PKA: 10.71±0.40(Predicted)
• CAS DataBase Reference: (1R,3s,5S)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3s,5S)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane(423165-07-5)
• EPA Substance Registry System: (1R,3s,5S)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane(423165-07-5)

Safety Data

• Hazardous Substances Data: 423165-07-5(Hazardous Substances Data)

Usage

Description

(1R,3s,5S)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, also known as a metabolite of Maraviroc, is an organic compound with off-white to pale yellow solid chemical properties. It is derived from the metabolism of Maraviroc, a drug used in the treatment of HIV.

Uses

Used in Pharmaceutical Industry:
(1R,3s,5S)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane is used as an intermediate compound for the synthesis of Maraviroc, a drug used in the treatment of HIV. Its role in the pharmaceutical industry is crucial for the development and production of Maraviroc, which helps in managing the symptoms and progression of HIV in patients.
Used in Research and Development:
In the field of research and development, (1R,3s,5S)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane serves as a valuable compound for studying the structure-activity relationships of Maraviroc and its analogs. This knowledge can be applied to design and develop new drugs with improved efficacy and safety profiles for the treatment of HIV and other related conditions.
Used in Quality Control and Analysis:
(1R,3s,5S)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane is also used in the quality control and analysis of Maraviroc and its formulations. Its presence as a metabolite can be monitored and quantified to ensure the purity, potency, and consistency of the drug, which is essential for maintaining the safety and efficacy of the medication.

InChI:InChI=1/C13H22N4/c1-8(2)13-16-15-9(3)17(13)12-6-10-4-5-11(7-12)14-10/h8,10-12,14H,4-7H2,1-3H3/t10-,11+,12+

Upstream product

• 1361964-33-1 C₂₀H₃₀N₄O 
• 376348-67-3 exo-N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-2-methylpropanamide 
• 76272-36-1 8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl-amine 
• 28957-72-4 N-benzyltropinone 
• 542-05-2 acetonedicarboxylic acid 
• 76272-34-9 8-benzyl-8-azabicyclo[3.2.1] octan-3-one oxime 
• 423165-13-3 exo-8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 

Downstream Products

• 376348-65-1 maraviroc 
• 1028333-37-0 (S)-d2-{3-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-aza-bicyclo[3.2.1]oct-8-yl]-1-phenyl-propyl}-carbamic acid tert-butyl ester 
• 1221569-04-5 1-acetyl-N-(3-chloro-4-methylphenyl)-N-(3-(3-exo-(3-isopropyl-5-methyl-4-hydro-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl)propyl)-4-piperidinylcarboxamide 
• 674782-29-7 maraviroc 
• 1370259-87-2 (4-{1-[benzyl(1-phenylethyl)amino]-3-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]-3-oxopropyl}phenyl)carbamic acid tert-butyl ester 
• 1370259-81-6 (4-{1-amino-3-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]propyl}phenyl)carbamic acid tert-butyl ester 
• 1370259-80-5 4,4-difluorocyclohexanecarboxamide N-{1-(4-aminophenyl)-3-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]propyl} 
• 1370259-96-3 4,4-difluorocyclohexanecarboxamide N-{1-(4-{2-[(7-aminoheptylcarbamoyl)methoxy]acetylamino}phenyl)-3-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]propyl} 
• 1370259-95-2 (7-{2-[(4-{1-(4,4-difluorocyclohexylcarbonylamino)-3-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]propyl}phenylcarbamoyl)methoxy]acetylamino}heptyl)carbamic acid benzyl ester 
• 1370259-79-2 C₄₅H₆₉F₂N₉O₇ 
• 1370259-90-7 (4-{1-(4,4-difluorocyclohexylcarbonylamino)-3-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]propyl}phenyl)carbamic acid tert-butyl ester 

Relevant articles and documents

METHOD FOR PREPARING MARAVIROC

Provided is a method for preparing a tropane derivative, maraviroc, including reacting a compound of formula (II) with a compound of formula (I), wherein the compound of formula (II) is prepared by the steps of acetylation of a compound of formula (III), activation and substitution of a compound of formula (IV) by a chlorination agent, cyclization of a compound of formula (V), and debenzylation of a compound of formula (VI) by hydrogenation. Hence, the present disclosure provides a method for preparing maraviroc with good yield and simple operation.

TRIAZOLYL TROPANE DERIVATIVES

This invention relates to novel triazolyl tropane derivatives, their acceptable acid addition salts, solvates, hydrates and polymorphs thereof. The invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions beneficially treated by blocking or reducing the binding ability of the CCR5 receptor.