N-benzyl-4-chloro-N-cyclohexylbenzaMide

Base Information

• Chemical Name: N-benzyl-4-chloro-N-cyclohexylbenzaMide
• CAS No.: 945714-67-0
• Molecular Formula: C20H22ClNO
• Molecular Weight: 327.84778
• Mol file: 945714-67-0.mol

Synonyms:N-benzyl-4-chloro-N-cyclohexylbenzaMide;4-Chloro-N-cyclohexyl-N-(phenylmethyl)benzamide

Chemical Property of N-benzyl-4-chloro-N-cyclohexylbenzaMide

Chemical Property:

• Boiling Point: 497.6±38.0 °C(Predicted)
• PKA: -1.54±0.20(Predicted)
• PSA: 20.31000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 5.31510
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 35 mg/ml) or in Ethanol (up to 20 mg/ml)

Purity/Quality:

97% ^*data from raw suppliers

FPS-ZM1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: FPS-ZM1 (945714-67-0) is a high-affinity RAGE (Receptor for Advanced Glycation End products) receptor antagonist (IC50?= 0.6 μM). It lowers levels of Aβ via binding to the V domain of RAGE and can block multiple mechanisms of Aβ40- and Aβ42-induced cellular stress in RAGE-expressing brain endothelium, neurons and microglia?in vitro?and?in vivo.1,2? Can cross the BBB.? In a rat model of intracerebral hemorrhage, FPS-ZM1 was able to attenuate blood-brain barrier and white matter fiber damage.3?FPS-ZM1 antagonism of RAGE was able to ameliorate inflammatory damage after acute intracerebral hemorrhage via downstream blockade of high mobility box-1(HMGB1) signaling.4? FPS-ZM1 has also been shown to impair breast cancer cell invasion and metastasis.5
• Uses: FPS-ZM1 is a blood-brain-barrier permeant blocker of RAGE V domain-mediated ligand binding (Ki?= 25, 148, & 230 nM, respectively, against Aβ40, HMGB1 & S100B, binding to sRAGE).

Technology Process of N-benzyl-4-chloro-N-cyclohexylbenzaMide

There total 3 articles about N-benzyl-4-chloro-N-cyclohexylbenzaMide 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:

N-benzylcyclohexylamine (4383-25-9) + 4-chloro-benzoyl chloride (122-01-0) → 4-chloro-N-cyclohexyl-N-(phenylmethyl)benzamide (945714-67-0)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2013.05.079

Reference yield:

cyclohexylamine (108-91-8,157973-60-9) → 4-chloro-N-cyclohexyl-N-(phenylmethyl)benzamide (945714-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanol / 3 h / 64 °C

1.2: 5 h / 20 - 64 °C

2.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere

With dmap; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; 1.1: |Borch Reduction / 1.2: |Borch Reduction;

DOI:10.1016/j.tet.2013.05.079

Reference yield:

benzaldehyde (100-52-7) → 4-chloro-N-cyclohexyl-N-(phenylmethyl)benzamide (945714-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanol / 3 h / 64 °C

1.2: 5 h / 20 - 64 °C

2.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere

With dmap; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; 1.1: |Borch Reduction / 1.2: |Borch Reduction;

DOI:10.1016/j.tet.2013.05.079

upstream raw materials:

cyclohexylamine

benzaldehyde

N-benzylcyclohexylamine

4-chloro-benzoyl chloride