1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione

Base Information

• Chemical Name: 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: 471.31
• Mol file: 1449413-23-3.mol

Synonyms:

Chemical Property of 1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione

Chemical Property:

• Boiling Point: 700.7±70.0 °C(Predicted)
• PKA: 11.10±0.40(Predicted)
• Density: 1.560±0.06 g/cm3(Predicted)

Purity/Quality:

99.9% ^*data from raw suppliers

1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• 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.

Technology Process of 1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione

There total 19 articles about 1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

C10H7BrN2O4*BrH + N-benzoylpiperazine hydrochloride (56227-55-5,79332-89-1) → 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)

Guidance literature:

C₁₀H₇BrN₂O₄*BrH; N-benzoylpiperazine hydrochloride; With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 5 ℃; Inert atmosphere; Large scale;

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In acetonitrile; at 5 - 25 ℃; Reagent/catalyst; Solvent; Inert atmosphere; Large scale;

DOI:10.1021/acs.oprd.7b00133

Reference yield: 93.7%

2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (954215-12-4) + N-benzoylpiperazine hydrochloride (56227-55-5,79332-89-1) → 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)

Guidance literature:

2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid; N-benzoylpiperazine hydrochloride; With 4-methyl-morpholine; In 1-methyl-pyrrolidin-2-one; at 20 - 25 ℃; for 1h; Inert atmosphere; Industrial scale;

With Diphenylphosphinic chloride; In 1-methyl-pyrrolidin-2-one; at 0 - 25 ℃; Reagent/catalyst; Solvent; Inert atmosphere; Industrial scale;

DOI:10.1021/acs.oprd.7b00133

Reference yield: 92.0%

C10H7BrN2O4*BrH + N-benzoylpiperazine hydrochloride (56227-55-5,79332-89-1) → 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) + (4-(diphenylphosphoryl)piperazin-1-yl)(phenyl)methanone

Guidance literature:

With N-ethyl-N,N-diisopropylamine; Diphenylphosphinic chloride; In acetonitrile; Inert atmosphere;

DOI:10.1021/acs.oprd.7b00133

upstream raw materials:

2-chloro-1-(1-(phenylsulfonyl)-1H-pyrrol-3-yl)ethanone

N1--benzenesulfonyl-4--methoxy--6--azainole N6-oxide

N1--benzenesulfonyl-7--bromo-4--methoxy--6--azainole

methyl 2-(7-bromo-4-methoxy-6-azaindol-3-yl)-2-oxoacetate