Bms-378806

Base Information

• Chemical Name: Bms-378806
• CAS No.: 357263-13-9
• Molecular Formula: C22H22N4O4
• Molecular Weight: 406.441
• UNII: IMN5E6PLUK
• Nikkaji Number: J2.933.501J
• Wikidata: Q27280796
• ChEMBL ID: CHEMBL337301
• Mol file: 357263-13-9.mol

Synonyms:4-benzoyl-1-((4-methoxy-1H- pyrrolo(2,3-b)pyridin-3-yl)oxoacetyl)-2- (R)-methylpiperazine;BMS-378806

Chemical Property of Bms-378806

Chemical Property:

• Vapor Pressure: 2.08E-15mmHg at 25°C
• Boiling Point: 622.3°Cat760mmHg
• Flash Point: 330.2°C
• PSA: 95.60000
• Density: 1.328g/cm³
• LogP: 2.00310
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥20.2 mg/mL in DMSO
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 406.16410520
• Heavy Atom Count: 30
• Complexity: 666

Purity/Quality:

98% min ^*data from raw suppliers

BMS806 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CN(CCN1C(=O)C(=O)C2=CNC3=NC=CC(=C23)OC)C(=O)C4=CC=CC=C4
• Isomeric SMILES: C[C@@H]1CN(CCN1C(=O)C(=O)C2=CNC3=NC=CC(=C23)OC)C(=O)C4=CC=CC=C4
• Description: BMS-806 is a small molecule that inhibits the first step of HIV-1 infection by blocking the binding of host cell CD4 with viral gp120 protein. It binds the exterior envelope glycoprotein gp120 (Kd= 21.1 nM; Ki = 24.9 nM), blocking the conformational change that occurs with CD4 binding and preventing fusion of the viral and target cell membranes. BMS-806 is specific to HIV-1 irrespective of chemokine receptor preference, with no activity against HIV-2, SIV, or a panel of additional viruses.
• Uses: BMS 806 is a small molecular inhibitor of HIV-1 virus which blocks the interaction between gp120 and CD4 cells.

Technology Process of Bms-378806

There total 11 articles about Bms-378806 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:

(2R)-methylpiperazine (75336-86-6) → 4-benzoyl-1-[(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2-(R)-methylpiperazine (357263-13-9)

Guidance literature:

Multi-step reaction with 6 steps

1: diethylaluminum chloride / CH₂Cl₂; hexane / 48 h / 20 °C

2: 81 percent / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; N,N-diisopropylethylamine / dimethylformamide / 8 h / 20 °C

3: 91 percent / mCPBA / acetone / 8 h

4: HNO₃; CF₃CO₂H / 8 h

5: methanol / 8 h / Heating

6: 5.7 g / PCl₃ / ethyl acetate / 8 h / 20 °C

With nitric acid; diethylaluminium chloride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; phosphorus trichloride; In methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm034082o

Reference yield:

4-benzoyl-1-[(4-methoxy-7-oxido-1H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2-(R)-methylpiperazine (357263-05-9) → 4-benzoyl-1-[(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2-(R)-methylpiperazine (357263-13-9)

Guidance literature:

With phosphorus trichloride; In ethyl acetate; at 20 ℃; for 8h;

DOI:10.1021/jm034082o

Reference yield:

4-benzoyl-2-(R)-methyl-1-[(4-nitro-7-oxido-1H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]piperazine (357262-96-5) → 4-benzoyl-1-[(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2-(R)-methylpiperazine (357263-13-9)

Guidance literature:

Multi-step reaction with 2 steps

1: MeONa

2: 85 mg / PCl₃ / ethyl acetate

With sodium methylate; phosphorus trichloride; In ethyl acetate;

DOI:10.1039/b415159c

upstream raw materials:

4-benzoyl-1-[(4-methoxy-7-oxido-1H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2-(R)-methylpiperazine

4-benzoyl-2-(R)-methyl-1-[(4-nitro-7-oxido-1H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]piperazine

benzoic acid methyl ester

7-Azaindole

Downstream raw materials:

(R)-N-(benzoyl)-3-methyl-N'-[(4-hydroxyl-7-azaindol-3-yl)-oxoacetyl]-piperazine

Refernces

• 1、 Wang, Tao,Zhang, Zhongxing,Wallace, Owen B.,Deshpande, Milind,Fang, Haiquan,Yang, Zheng,Zadjura, Lisa M.,Tweedie, Donald L.,Huang, Stella,Zhao, Fang,Ranadive, Sunanda,Robinson, Brett S.,Gong, Yi-Fei,Ricarrdi, Keith,Spicer, Timothy P.,Deminie, Carol,Rose, Ronald,Wang, Hwei-Gene Heidi,Blair, Wade S.,Shi, Pei-Yong,Lin, Pin-Fang,Colonno, Richard J.,Meanwell, Nicholas A.. "Discovery of 4-benzoyl-1-[(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2-(R) -methylpiperazine (BMS-378806): A novel HIV-1 attachment inhibitor that interferes with CD4-gp120 interactions". . p. 4236 - 4239. Retrieved 2007/10/03.
• 2、 -. "Antiviral azaindole derivatives". . . Retrieved 2008/06/13.