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

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 
• 76272-36-1 8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl-amine 
• 79-30-1 isobutyryl chloride 
• 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 
• 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.

Asymmetric Mannich Reaction and Construction of Axially Chiral Sulfone-Containing Styrenes in One Pot from α-Amido Sulfones Based on the Waste-Reuse Strategy

A simultaneous asymmetric Mannich reaction and the construction of axially chiral sulfone-containing styrenes in one pot from α-amido sulfones based on the waste-reuse strategy was demonstrated. A series of chiral β-amino diesters and axially chiral sulfone-containing styrenes with various functional groups were synthesized in good to excellent yields and enantioselectivities under mild conditions. In addition, this protocol has been successfully applied to synthesize the anti-HIV drug Maraviroc and chiral trichloro derivatives.

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.

AMIDE COMPOUNDS, THEIR PHARMACEUTICAL COMPOSITIONS, THEIR PREPARATION METHOD AND THEIR USES

The present invention pertains to the field of pharmaceutical chemistry and discloses 8-(3-aminopropyl)-3-exo-8-azabicyclo[3.2.1]octane-3-amino amide compounds represented by formula I, the pharmaceutical compositions, the preparation method and the use thereof. Such compounds or pharmaceutically acceptable salts thereof can be used as an antagonist of CCR5 in preparing medicaments for treating diseases mediated by CCR5, particularly HIV infection, asthma, rheumatoid arthritis, autoimmune diseases and chronic obstructive pulmonary diseases (COPD).

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.

PREPARATION AND UTILITY OF CCR5 INHIBITORS

Disclosed herein are substituted 8-azabicyclo[3.2.1]octane-based anti-infective agents of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

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.

Development of a bulk enabling route to maraviroc (UK-427,857), a CCR-5 receptor antagonist

A bulk enabling synthesis of the CCR-5 receptor antagonist, Maraviroc (UK-427,857) (1), is presented. Synthesis of the three key fragments, β-amino ester 3,4,4-difluorohexanecarboxylic acid (2), and 1,3,4-triazole-substituted tropane fragment 4 are described. Coupling strategies for these fragments are discussed and described, including synthetic challenges, protection strategies, impurity generation, and final scale-up of the developed route to 1.