Urea, N-[5-chloro-2-[2-[(2R)-4-[(4-fluorophenyl)Methyl]-2-Methyl-1-piperazinyl]-2-oxoethoxy]phenyl]-

Base Information

• Chemical Name: Urea, N-[5-chloro-2-[2-[(2R)-4-[(4-fluorophenyl)Methyl]-2-Methyl-1-piperazinyl]-2-oxoethoxy]phenyl]-
• CAS No.: 217645-70-0
• Molecular Formula: C21H24ClFN4O3
• Molecular Weight: 434.89200
• Mol file: 217645-70-0.mol

Synonyms:BX471;BX-471 free base;UNII-76K17ZG4ZN;

Chemical Property of Urea, N-[5-chloro-2-[2-[(2R)-4-[(4-fluorophenyl)Methyl]-2-Methyl-1-piperazinyl]-2-oxoethoxy]phenyl]-

Chemical Property:

• Boiling Point: 593.5±50.0 °C(Predicted)
• PKA: 13.66±0.70(Predicted)
• PSA: 88.89000
• Density: 1.346±0.06 g/cm3(Predicted)
• LogP: 3.54400
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥25mg/mL

Purity/Quality:

97% ^*data from raw suppliers

BX 471 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Description: The CC chemokine receptor-1 (CCR1), whose ligands include macrophage inflammatory protein-1α (MIP-1α), RANTES, and monocyte chemotactic protein-3 (MCP-3), has a central role in leukocyte trafficking and is highly expressed in certain autoimmune diseases. BX 471 is a nonpeptide CCR1 antagonist that has been shown to displace MIP-1α, RANTES, and MCP-3 with Ki values of 1, 2.8, and 5.5 nM, respectively. It demonstrates >10,000-fold selectivity for CCR1 over 28 additional G protein-coupled receptors, including related chemokine receptors. In a rat experimental allergic encephalomyelitis model of multiple sclerosis, BX 471 at 50 mg/kg was shown to significantly reduce the severity of the disease. BX 471 also decreases the inflammatory response during sepsis, blocks migration of monocytes isolated from rheumatoid arthritis patients, and prevents macrophage and T-cell recruitment in a mouse model of lupus nephritis.
• Uses: BX471 has been used in chemotaxis assay to study the responses of HEK293 cells expressing human C-C motif chemokine receptor 1 (CCR1) to CC motif ligand 3 (CCL3)-induced cell migration. It has also been used as a CCR1 inhibitor to assess the effects of CCR1 on the migration and epithelial-mesenchymal transition (EMT).

Technology Process of Urea, N-[5-chloro-2-[2-[(2R)-4-[(4-fluorophenyl)Methyl]-2-Methyl-1-piperazinyl]-2-oxoethoxy]phenyl]-

There total 6 articles about Urea, N-[5-chloro-2-[2-[(2R)-4-[(4-fluorophenyl)Methyl]-2-Methyl-1-piperazinyl]-2-oxoethoxy]phenyl]- 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: 52.0%

1-(5-chloro-2-{2-[(2R)-2-methylpiperazin-1-yl]-2-oxoethoxy}phenyl)urea (683202-95-1) + 1-chloromethyl-4-fluorobenzene (352-11-4) → 1-(5-chloro-2-{2-[(2R)-4-(4-fluorobenzyl)-2-methylpiperazin-1-yl]-2-oxoethoxy}phenyl)urea (217645-70-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; sodium iodide; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1002/jlcr.1023

Reference yield: 51.0%

1-(5-chloro-2-{2-[(2S)-2-methylpiperazin-1-yl]-2-oxoethoxy}phenyl)urea + 1-chloromethyl-4-fluorobenzene (352-11-4) → 1-(5-chloro-2-{2-[(2S)-4-(4-fluorobenzyl)-2-methylpiperazin-1-yl]-2-exoethoxy}-phenyl) urea (217645-70-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; sodium iodide; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1002/jlcr.1023

Reference yield:

2-chloro-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone (422270-30-2) + 1-(2-Hydroxy-5-chlorophenyl)urea (57718-28-2) → 1-(5-chloro-2-{2-[(2R)-4-(4-fluorobenzyl)-2-methylpiperazin-1-yl]-2-oxoethoxy}phenyl)urea (217645-70-0)

Guidance literature:

upstream raw materials:

1-(5-chloro-2-{2-[(2R)-2-methylpiperazin-1-yl]-2-oxoethoxy}phenyl)urea

1-chloromethyl-4-fluorobenzene

2-chloro-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone

1-(2-Hydroxy-5-chlorophenyl)urea