Temsavir

Base Information

• Chemical Name: Temsavir
• CAS No.: 701213-36-7
• Molecular Formula: C24H23N7O4
• Molecular Weight: 473.491
• UNII: 4B6J53W8N3
• ChEMBL ID: CHEMBL3301620
• DSSTox Substance ID: DTXSID20462146
• Metabolomics Workbench ID: 144575
• NCI Thesaurus Code: C152553
• Nikkaji Number: J3.318.366F
• Wikidata: Q27259369
• Mol file: 701213-36-7.mol

Synonyms:BMS-626529

Chemical Property of Temsavir

Chemical Property:

• Boiling Point: 787.6±70.0 °C(Predicted)
• PKA: 10.92±0.40(Predicted)
• PSA: 126.31000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: 1.50370
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 473.18115224
• Heavy Atom Count: 35
• Complexity: 799

Purity/Quality:

97% ^*data from raw suppliers

Temsavir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN(C=N1)C2=NC=C(C3=C2NC=C3C(=O)C(=O)N4CCN(CC4)C(=O)C5=CC=CC=C5)OC
• Recent ClinicalTrials: Absolute Bioavailability of BMS-626529 After Oral and Intravenous Dosing
• Description: BMS 626529 is an inhibitor of HIV-1 attachment. It binds to non-ligand bound HIV-1 gp120 to inhibit HIV-1 interaction with host CD4+ T cells and subsequent HIV-1 binding and cell entry. BMS 626529 reduces infectivity of laboratory strains and clinical isolates of HIV-1 (EC50s = 0.4-2,000 and 25-2,000 nM, respectively) with cytotoxic concentration (CC50) values greater than 100 μM in a panel of mammalian cell lines.
• Uses: Temsavir is a Fostemsavir (CAS# 864953-29-7) intermediate and an antiviral agent. It is an HIV-1 attachment inhibitor.

Technology Process of Temsavir

There total 23 articles about Temsavir 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: 82.6%

methyl 2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (701214-00-8) + N-benzoylpiperazine hydrochloride (56227-55-5,79332-89-1) → 1-(4-benzoylpiperazin-1-yl)-2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-ethane-1,2-dione (701213-36-7)

Guidance literature:

With sodium t-butanolate; In tetrahydrofuran; N,N-dimethyl-formamide; at 17 - 20 ℃; for 1h;

Reference yield: 77.5%

3-methyl-1H-[1,2,4]triazole (7170-01-6) + C22H19F3N4O7S → 1-(4-benzoylpiperazin-1-yl)-2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-ethane-1,2-dione (701213-36-7)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In toluene; for 4h; Reflux;

Reference yield: 68.0%

2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid sodium salt + N-benzoylpiperazine hydrochloride (56227-55-5,79332-89-1) → 1-(4-benzoylpiperazin-1-yl)-2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-ethane-1,2-dione (701213-36-7)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 - 40 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.8b00759

upstream raw materials:

methyl 2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate

N-benzoylpiperazine hydrochloride

2-acetylamino-4-methylpyridine

N-(5-bromo-4-methylpyridin-2-yl)acetamide

Downstream raw materials:

1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium (3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl hydrogen phosphate