Nps-2143

Base Information

• Chemical Name: Nps-2143
• CAS No.: 284035-33-2
• Molecular Formula: C₂₄H₂₅ClN₂O₂
• Molecular Weight: 408.928
• UNII: Z25PJ77W7V
• DSSTox Substance ID: DTXSID10426075
• Nikkaji Number: J3.351.731I
• Wikipedia: NPS-2143
• Wikidata: Q20707377
• Pharos Ligand ID: AMQ826YYZXZ6
• Metabolomics Workbench ID: 149547
• ChEMBL ID: CHEMBL180672
• Mol file: 284035-33-2.mol

Synonyms:N-((R)-2-hydroxy-3-(2-cyano-3-chlorophenoxy)propyl)-1,1-dimethyl-2-(2-nephthyl)ethylamine;N-(2-hydroxy-3-(2-cyano-3-chlorophenoxy)propyl)-1,1-dimethyl-2-(2-nephthyl)ethylamine;NPS 2143;NPS2143

Chemical Property of Nps-2143

Chemical Property:

• Vapor Pressure: 1.17E-15mmHg at 25°C
• Refractive Index: 1.631
• Boiling Point: 608.4 °C at 760 mmHg
• PKA: 13.67±0.20(Predicted)
• Flash Point: 321.8 °C
• PSA: 65.28000
• Density: 1.23 g/cm³
• LogP: 5.10638
• Storage Temp.: Desiccate at RT
• Solubility.: ≥40.9 mg/mL in DMSO; insoluble in H2O; ≥28.35 mg/mL in EtOH
• XLogP3: 5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 408.1604557
• Heavy Atom Count: 29
• Complexity: 560

Purity/Quality:

99% ^*data from raw suppliers

NPS 2143 hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(CC1=CC2=CC=CC=C2C=C1)NCC(COC3=C(C(=CC=C3)Cl)C#N)O
• Isomeric SMILES: CC(C)(CC1=CC2=CC=CC=C2C=C1)NC[C@H](COC3=C(C(=CC=C3)Cl)C#N)O
• Uses: NPS 2143 acts as a potent and selective antagonist for CaSR (Calcium-sensing receptor) which is involved in calcium blood concentration homeostasis.

Technology Process of Nps-2143

There total 22 articles about Nps-2143 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: 73.0%

C10H8ClNO2 + [2-methyl-1-(naphthalen-2-yl)propan-2-yl]amine (198226-63-0) → 2-Chloro-6-[(S)-3-(1,1-dimethyl-2-naphthalen-2-yl-ethylamino)-2-hydroxy-propoxy]-benzonitrile (284035-33-2)

Guidance literature:

In ethanol; at 80 ℃; for 72h; Sealed tube;

DOI:10.3390/ijms221810124

Reference yield:

C10H8ClNO2 + 2-methyl-1-(naphthalen-2-yl)propan-2-amine hydrochloride (351490-95-4) → 2-Chloro-6-[(S)-3-(1,1-dimethyl-2-naphthalen-2-yl-ethylamino)-2-hydroxy-propoxy]-benzonitrile (284035-33-2)

Guidance literature:

With trialkylamine; In ethanol; for 7h; Reflux;

DOI:10.1038/s41429-019-0177-9

Reference yield:

1-(naphthalen-2-ylmethyl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate → NPS 2143 (284035-33-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / various solvent(s); methanol / 0 °C

1.2: dimethylsulfoxide / 70 °C

2.1: 0.95 g / hydrogen / Pd/C / ethanol

3.1: ethanol / 60 °C

With hydrogen; sodium hydride; palladium on activated charcoal; In methanol; ethanol;

DOI:10.1016/j.tetasy.2005.07.022

upstream raw materials:

[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amine

2-chloro-6-([(2R)-2-oxiranylmethyl]oxy)benzonitrile

2-(2-methyl-2-nitropropyl)naphthalene

(+/-)-2-chloro-6-(3-chloro-2-hydroxypropoxy)benzonitrile

Refernces

• 1、 Chen, Yao,Ju, Yuan,Li, Chungen,Yang, Tao,Deng, Yong,Luo, Youfu. "Design, synthesis, and antibacterial evaluation of novel derivatives of NPS-2143 for the treatment of methicillin-resistant S. aureus (MRSA) infection". . p. 545 - 554. Retrieved 2019/04/10.
• 2、 Kamal, Ahmed,Chouhan, Gagan. "Chemoenzymatic synthesis of calcilytic agent NPS-2143 employing a lipase-mediated resolution protocol". . p. 2784 - 2789. Retrieved 2007/10/03.