4-[4-(4'-Chlorobiphenyl-2-ylmethyl)piperazin-1-YL]benzoic acid

Base Information

• Chemical Name: 4-[4-(4'-Chlorobiphenyl-2-ylmethyl)piperazin-1-YL]benzoic acid
• CAS No.: 916204-05-2
• Molecular Formula: C24H23ClN2O2
• Molecular Weight: 406.912
• DSSTox Substance ID: DTXSID40700734
• Wikidata: Q72517480
• Mol file: 916204-05-2.mol

Synonyms:916204-05-2;4-[4-(4'-CHLOROBIPHENYL-2-YLMETHYL)PIPERAZIN-1-YL]BENZOIC ACID;4-(4-((4'-CHLORO-[1,1'-BIPHENYL]-2-YL)METHYL)PIPERAZIN-1-YL)BENZOIC ACID;4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]benzoic acid;4-[4-(4'-Chloro-2-biphenylylmethyl)-1-piperazinyl]benzoic acid;4-[4-(4'-Chlorobiphenyl-2-ylmethyl)piperazin-1-yl]benzoicAcid-d8;4-[4-[(4'-Chloro[1,1'-biphenyl]-2-yl)methyl]-1-piperazinyl]benzoic Acid;C24H23ClN2O2;SCHEMBL1741405;DTXSID40700734;MFCD16251290;AS-42094;FT-0664558;4-(4-((4'-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)benzoic acid;4-(4-((4'-chloro-1,1'-biphenyl-2-yl)methyl)-1-piperazinyl)benzoic acid;4-{4-[(4'-Chloro[1,1'-biphenyl]-2-yl)methyl]piperazin-1-yl}benzoic acid;4-(4-((4'-CHLORO-[1,1'-BIPHENYL]-2-YL)METHYL)PIPERAZIN-1-YL)BENZOICACID

Chemical Property of 4-[4-(4'-Chlorobiphenyl-2-ylmethyl)piperazin-1-YL]benzoic acid

Chemical Property:

• PSA: 43.78000
• LogP: 5.03030
• Solubility.: Dimethylformamide, DMSO, Methanol
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 406.1448057
• Heavy Atom Count: 29
• Complexity: 521

Purity/Quality:

>98% ^*data from raw suppliers

4-[4-(4''-Chlorobiphenyl-2-ylmethyl)piperazin-1-yl]benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CC2=CC=CC=C2C3=CC=C(C=C3)Cl)C4=CC=C(C=C4)C(=O)O
• Uses: 4-[4-(4''-Chlorobiphenyl-2-ylmethyl)piperazin-1-yl]benzoic Acid is an intermediate in the production of ABT 737 (A112550), which is a selective inhibitor of BCL-2, in small cell lung cancer. ABT-737 induced dramatic regressions in tumors derived from some SCLC cell lines. Potent Bcl-2 Family inhibitor.

Technology Process of 4-[4-(4'-Chlorobiphenyl-2-ylmethyl)piperazin-1-YL]benzoic acid

There total 9 articles about 4-[4-(4'-Chlorobiphenyl-2-ylmethyl)piperazin-1-YL]benzoic acid 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: 93.0%

4-[4-(4'-chloro-biphenyl-2-ylmethyl)-piperazin-1-yl]-benzoic acid ethyl ester (926934-07-8) → 4-(4-((4'-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)benzoic acid (916204-05-2)

Guidance literature:

4-[4-(4'-chloro-biphenyl-2-ylmethyl)-piperazin-1-yl]-benzoic acid ethyl ester; With lithium hydroxide monohydrate; water; In 1,4-dioxane; at 95 ℃;

With hydrogenchloride; In water;

Reference yield:

ethyl 4-(piperazin-1-yl)benzoate (80518-57-6) → 4-(4-((4'-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)benzoic acid (916204-05-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / sodium triacetoxyborohydride / 1,2-dichloro-ethane / 1.25 h

2: 73 percent / aq. Na₂CO₃ / PdCl₂(PPh₃)2 / ethanol; 1,2-dimethoxy-ethane / 4.5 h / 90 °C

3: lithium hydroxide monohydrate / tetrahydrofuran; methanol; H₂O / 16 h

With lithium hydroxide; sodium tris(acetoxy)borohydride; sodium carbonate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; water; 1,2-dichloro-ethane; 2: Suzuki coupling;

DOI:10.1021/jm061152t

Reference yield:

4-[4-(2-bromo-benzyl)-piperazin-1-yl]-benzoic acid ethyl ester (926934-01-2) → 4-(4-((4'-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)benzoic acid (916204-05-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / aq. Na₂CO₃ / PdCl₂(PPh₃)2 / ethanol; 1,2-dimethoxy-ethane / 4.5 h / 90 °C

2: lithium hydroxide monohydrate / tetrahydrofuran; methanol; H₂O / 16 h

With lithium hydroxide; sodium carbonate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; water; 1: Suzuki coupling;

DOI:10.1021/jm061152t

upstream raw materials:

4-[4-(4'-chloro-biphenyl-2-ylmethyl)-piperazin-1-yl]-benzoic acid ethyl ester

4-[4-(2-bromo-benzyl)-piperazin-1-yl]-benzoic acid ethyl ester

ethyl 4-(piperazin-1-yl)benzoate

ortho-bromobenzaldehyde

Downstream raw materials:

ABT-737

4-{4-[(4'-chlorobiphenyl-2-yl)methyl]piperazin-1-yl}-N-({[(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methyl}sulfonyl)benzamide

C₄₀H₄₉ClN₄O₄S

C₃₉H₄₇ClN₄O₄S

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