2-(4-Chloro-3-(3-(1-hydroxycycloheptyl)propanoyl)phenyl)-4-((2R)-2-hydroxy-3-methoxy-propyl)-1,2,4-triazine-3,5-dione

Base Information

• Chemical Name: 2-(4-Chloro-3-(3-(1-hydroxycycloheptyl)propanoyl)phenyl)-4-((2R)-2-hydroxy-3-methoxy-propyl)-1,2,4-triazine-3,5-dione
• CAS No.: 724424-43-5
• Molecular Formula: C₂₂H₂₉ClN₄O₆
• Molecular Weight: 480.948
• UNII: T8B02RAU3C
• ChEMBL ID: CHEMBL1823817
• DSSTox Substance ID: DTXSID20222742
• Metabolomics Workbench ID: 153161
• Nikkaji Number: J3.488.791H
• Wikidata: Q27088319
• Mol file: 724424-43-5.mol

Synonyms:CE 224,535;CE 224535;CE-224,535;CE-224535;CE224,535;CE224535

Chemical Property of 2-(4-Chloro-3-(3-(1-hydroxycycloheptyl)propanoyl)phenyl)-4-((2R)-2-hydroxy-3-methoxy-propyl)-1,2,4-triazine-3,5-dione

Chemical Property:

• PKA: 13.48±0.20(Predicted)
• PSA: 139.17000
• Density: 1.47g/cm3
• LogP: 1.53230
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 480.1775624
• Heavy Atom Count: 33
• Complexity: 742

Purity/Quality:

98% ^*data from raw suppliers

2-CHLORO-N-[(1-HYDROXYCYCLOHEPTYL)METHYL]-5-[4-[(2R)-2-HYDROXY-3-METHOXYPROPYL]-3,5-DIOXO-1,2,4-TRIAZIN-2-YL]BENZAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCC(CN1C(=O)C=NN(C1=O)C2=CC(=C(C=C2)Cl)C(=O)NCC3(CCCCCC3)O)O
• Isomeric SMILES: COC[C@@H](CN1C(=O)C=NN(C1=O)C2=CC(=C(C=C2)Cl)C(=O)NCC3(CCCCCC3)O)O
• Recent ClinicalTrials: Study of CE-224,535 A Twice Daily Pill To Control Rheumatoid Arthritis In Patients Who Have Not Totally Improved With Methotrexate
• Recent EU Clinical Trials: 'ESTUDIO DE FASE 2A ALEATORIZADO, DOBLE CIEGO, CONTROLADO CON PLACEBO Y DE GRUPOS PARALELOS DE CE-224,535, UN ANTAGONISTA DEL RECEPTOR P2X7, EN EL TRATAMIENTO DE LOS SIGNOS Y SíNTOMAS DE LA ARTRITIS REUMATOIDE EN PACIENTES CON UN CONTROL INADECUADO CON METROTEXATO'
• Uses: CE-224535, is a selective P2X7 receptor antagonist.

Technology Process of 2-(4-Chloro-3-(3-(1-hydroxycycloheptyl)propanoyl)phenyl)-4-((2R)-2-hydroxy-3-methoxy-propyl)-1,2,4-triazine-3,5-dione

There total 8 articles about 2-(4-Chloro-3-(3-(1-hydroxycycloheptyl)propanoyl)phenyl)-4-((2R)-2-hydroxy-3-methoxy-propyl)-1,2,4-triazine-3,5-dione 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: 74.0%

2-chloro-5-(3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-N-(1-hydroxy-cycloheptylmethyl)-benzamide + R(-)-glycidyl methyl ether (64491-70-9) → CE-224,535 (724424-43-5)

Guidance literature:

In DMF (N,N-dimethyl-formamide); at 80 ℃; for 17h; Product distribution / selectivity;

Reference yield:

5-{4-[2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl}-2-chloro-benzoic acid + 1-(aminomethyl)cycloheptanol (45732-95-4) → CE-224,535 (724424-43-5)

Guidance literature:

5-{4-[2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl}-2-chloro-benzoic acid; With 4-methyl-morpholine; dmap; 1,3,5-trichloro-2,4,6-triazine; In dichloromethane; at 0 - 20 ℃; for 4h;

1-(aminomethyl)cycloheptanol; In dichloromethane; at 20 ℃;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; for 40h;

Reference yield:

C11H6ClN3O6 (524712-40-1) → CE-224,535 (724424-43-5)

Guidance literature:

Multi-step reaction with 4 steps

1: mercaptoacetic acid; sodium hydroxide / water / 175 °C

2: oxalyl dichloride / dichloromethane

3: sodium hydroxide

4: N,N-dimethyl-formamide

With oxalyl dichloride; mercaptoacetic acid; sodium hydroxide; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.04.077

upstream raw materials:

R(-)-glycidyl methyl ether

1-(aminomethyl)cycloheptanol

(R^*,R^*)-α-Methyloxiranemethanol

C₁₁H₆ClN₃O₆