1449413-23-3

Basic information

• Product Name: 1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione
• Synonyms: 1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione
• CAS NO: 1449413-23-3
• Molecular Formula: C21H19BrN4O4
• Molecular Weight: 471.30396
• Mol File: 1449413-23-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 700.7±70.0 °C(Predicted)
• Appearance: /
• Density: 1.560±0.06 g/cm3(Predicted)
• PKA: 11.10±0.40(Predicted)
• CAS DataBase Reference: 1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione(1449413-23-3)
• EPA Substance Registry System: 1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione(1449413-23-3)

Safety Data

• Hazardous Substances Data: 1449413-23-3(Hazardous Substances Data)

Usage

Uses

1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione is a Fostemsavir (864953-29-7) intermediate and an antiviral agent. It is also involved in the synthesis of the HIV-1 attachment inhibitor pro-drug, BMS-663068.

Upstream product

• 954215-12-4 2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid 
• 13754-38-6 N-Benzoylpiperazine 
• 56227-55-5 N-benzoylpiperazine hydrochloride 
• 1421517-99-8 N1--benzenesulfonyl-4-methoxy-6--azainole 
• 954215-11-3 methyl 2-(7-bromo-4-methoxy-6-azaindol-3-yl)-2-oxoacetate 
• 1421517-89-6 N1--benzenesulfonyl-7--bromo-4--methoxy--6--azainole 
• 1421517-98-7 N1--benzenesulfonyl-4--methoxy--6--azainole N6-oxide 
• 91579-92-9 2-chloro-1-(1-(phenylsulfonyl)-1H-pyrrol-3-yl)ethanone 

Relevant articles and documents

Preparation of the HIV Attachment Inhibitor BMS-663068. Part 6. Friedel-Crafts Acylation/Hydrolysis and Amidation

The development of a process for appending the oxalyl amide side chain to the azaindole core of the HIV-attachment inhibitor BMS-663068 is described. A Friedel-Crafts acylation installed the oxalyl ester, which was subsequently hydrolyzed and amidated with a benzoyl piperazine. The development of the commercial route necessitated several key changes to the initial synthesis. For instance, in the original acylation process, nitromethane, a commonly used, but highly energetic cosolvent, was employed which was eventually replaced by catalytic tetra-n-butylammonium bisulfate to overcome gelling issues encountered during the reaction when nitromethane was omitted. It was further demonstrated that the amidation sequence could be relegated to a single-pot, homogeneous transformation through the use of the cost-effective coupling reagent diphenylphosphinic chloride. The above modifications have been utilized in multiple campaigns and reproducibly demonstrated on scales of up to 200 kg input.

Synthesis of the 6-azaindole containing HIV-1 attachment inhibitor pro-drug, BMS-663068

The development of a short and efficient synthesis of a complex 6-azaindole, BMS-663068, is described. Construction of the 6-azaindole core is quickly accomplished starting from a simple pyrrole, via a regioselective Friedel.Crafts acylation, Pictet.Spengler cyclization, and a radical-mediated aromatization. The synthesis leverages an unusual heterocyclic Noxide α-bromination to functionalize a critical C.H bond, enabling a highly regioselective copper-mediated Ullmann. Goldberg.Buchwald coupling to install a challenging triazole substituent. This strategy resulted in an efficient 11 step linear synthesis of this complex clinical candidate.