376348-67-3

Basic information

• Product Name: N-(8-Benzyl-8-azabicyclo[3.2.1]oct-3-yl-exo)-2-methylpropanamide
• Synonyms: N-(8-Benzyl-8-azabicyclo[3.2.1]oct-3-yl-exo)-2-methylpropanamide;exo-N-(8-Benzyl-8-azabicyclo[3.2.1]octan-3-yl)isobutyraMide;2-Methyl-N-[(3-exo)-8-(phenylMethyl)-8-azabicyclo[3.2.1]oct-3-yl]-propanaMide;N-((1R,3s,5S)-8-Benzyl-8-azabicyclo[3.2.1]octan-3-yl)isobutyraMide;N-(8-benzyl-8-azabicyclo [3.2.1] octan-3-yl)-2-methyl-propanamide
• CAS NO: 376348-67-3
• Molecular Formula: C₁₈H₂₆N₂O
• Molecular Weight: 286.41
• EINECS: 1533716-785-6
• Product Categories: Aromatics;Heterocycles;Intermediates
• Mol File: 376348-67-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 138-140 °C
• Boiling Point: 449.068 °C at 760 mmHg
• Flash Point: 225.388 °C
• Appearance: Light yellow solid
• Density: 1.09 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane
• PKA: 15.65±0.20(Predicted)
• CAS DataBase Reference: N-(8-Benzyl-8-azabicyclo[3.2.1]oct-3-yl-exo)-2-methylpropanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(8-Benzyl-8-azabicyclo[3.2.1]oct-3-yl-exo)-2-methylpropanamide(376348-67-3)
• EPA Substance Registry System: N-(8-Benzyl-8-azabicyclo[3.2.1]oct-3-yl-exo)-2-methylpropanamide(376348-67-3)

Safety Data

• Hazardous Substances Data: 376348-67-3(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Solid

InChI:InChI=1/C18H26N2O/c1-13(2)18(21)19-15-10-16-8-9-17(11-15)20(16)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,19,21)

Upstream product

• 132259-54-2 exo-(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-carbamic acid tert-butyl ester 
• 76272-34-9 8-Benzyl-1αH,5αH-nortropan-3-one Oxime 
• 28957-72-4 N-benzyltropinone 
• 100-46-9 benzylamine 
• 542-05-2 acetonedicarboxylic acid 
• 76272-34-9 8-benzyl-8-azabicyclo[3.2.1] octan-3-one oxime 
• 79-30-1 isobutyryl chloride 
• 76272-36-1 8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl-amine 
• 513-36-0 isobutyryl chloride 

Downstream Products

• 423165-13-3 exo-8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 
• 423165-07-5 UK-408027 
• 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 
• 376348-65-1 4,4-difluoro-N-[(1S)-3-[(1R,5S)-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide 
• 1545932-86-2 3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]octane p-toluenesulfonic acid salt 
• 376348-65-1 maraviroc 
• 376348-71-9 (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-phenylpropan-1-amine 
• 423165-08-6 exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate 
• 1519003-78-1 C₅₅H₈₁N₉O₈ 
• 1519003-85-0 C₃₀H₄₆N₈O₄ 
• 1519003-75-8 C₃₃H₅₂N₈O 
• 376348-70-8 tert-butyl (1S)-3-[3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropylcarbamate 
• 1361964-33-1 C₂₀H₃₀N₄O 

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.

Preparation and activities of macromolecule conjugates of the CCR5 antagonist maraviroc

CCR5 antagonists are among the most advanced approaches in HIV therapy and may also be relevant to treatment of graft-versus-host disease and Staphylococcus aureus infection. To expand the potential of the only approved CCR5 antagonist, Maraviroc, we studied derivatives that would enable functional linkage of Maraviroc to long-lived carriers. Through targeted synthesis, we discovered an effective linkage site on Maraviroc and demonstrate the potential of these derivatives to prepare potent chemically programmed antibodies and PEGylated derivatives. The resulting compounds effectively neutralized a variety of HIV-1 isolates. Both chemically programmed antibody and PEGylation approaches extend the neutralization activity of serum circulating Maraviroc. Derivation of a successful conjugation strategy for Maraviroc should further enable its use in chemically programmed vaccines, novel bispecific antibodies, and topical microbicides.

Asymmetric synthesis of maraviroc (UK-427,857)

The asymmetric synthesis of Maraviroc (UK-427,857), a chemochine receptor 5 (CCR-5) receptor antagonist, based on an expeditious organocatalytic enantioselective assembly of the chiral βamino aldehyde key fragment is presented. The reactions were performed on a gram-scale and allow for the rapid construction of new Maraviroc analogues.