1545932-86-2

Basic information

• Product Name: 3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]octane p-toluenesulfonic acid salt
• CAS NO: 1545932-86-2
• Molecular Weight: 406.549
• Mol File: 1545932-86-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]octane p-toluenesulfonic acid salt(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]octane p-toluenesulfonic acid salt(1545932-86-2)
• EPA Substance Registry System: 3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]octane p-toluenesulfonic acid salt(1545932-86-2)

Safety Data

• Hazardous Substances Data: 1545932-86-2(Hazardous Substances Data)

Upstream product

• 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 
• 76272-34-9 8-Benzyl-1αH,5αH-nortropan-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 
• 104-15-4 toluene-4-sulfonic acid 
• 28957-72-4 N-benzylnortropinone 
• 132259-54-2 exo-(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-carbamic acid tert-butyl ester 

Downstream Products

• 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 
• 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 
• 1519003-75-8 C₃₃H₅₂N₈O 
• 1519003-85-0 C₃₀H₄₆N₈O₄ 
• 1519003-78-1 C₅₅H₈₁N₉O₈ 
• 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 

Relevant articles and documents

Process research and scale-up of a commercialisable route to maraviroc (UK-427,857), a CCR-5 receptor antagonist

A six-step synthetic route to the CCR-5 receptor antagonist, Maraviroc (UK-427,857) (1) has been developed and demonstrated at scale in a pilot plant. The route has supported four Pilot-Plant campaigns and has produced multikilogram quantities of 1. Continued development of the synthetic route has resulted in a robust process with improved throughput compared to that of the original synthesis (Haycock-Lewandowski, S. J.; Mawby, N. J.; Wilder, A.; Ahman, J. Org. Process Res. Dev. 2008, 12, 1094-1103).

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.

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.