Sapitinib

Base Information

• Chemical Name: Sapitinib
• CAS No.: 848942-61-0
• Molecular Formula: C₂₃H₂₅ClFN₅O₃
• Molecular Weight: 473.935
• European Community (EC) Number: 642-427-0,935-731-2
• UNII: 3499328002
• ChEMBL ID: CHEMBL2408045
• DSSTox Substance ID: DTXSID50233942
• Metabolomics Workbench ID: 153217
• NCI Thesaurus Code: C77887
• Pharos Ligand ID: 26P3748YRDBK
• Wikidata: Q27088689
• Mol file: 848942-61-0.mol

Synonyms:AZD 8931;AZD-8931;AZD8931;sapitinib

Chemical Property of Sapitinib

Chemical Property:

• Boiling Point: 632.8±55.0 °C(Predicted)
• PKA: 16.17±0.46(Predicted)
• PSA: 92.10000
• Density: 1.339
• LogP: 4.61490
• Solubility.: ≥23.7 mg/mL in DMSO; insoluble in H2O; ≥57.8 mg/mL in EtOH with gentle warming
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 473.1629955
• Heavy Atom Count: 33
• Complexity: 641

Purity/Quality:

98% ^*data from raw suppliers

Sapitinib(AZD8931) 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(=O)CN1CCC(CC1)OC2=C(C=C3C(=C2)C(=NC=N3)NC4=C(C(=CC=C4)Cl)F)OC
• Recent ClinicalTrials: SAFIR02_Lung - Efficacy of Targeted Drugs Guided by Genomic Profiles in Metastatic NSCLC Patients
• Recent EU Clinical Trials: Evaluation of the efficacy of high throughput genome analysis as a therapeutic decision tool for patients with metastatic non small cell lung cancer

Technology Process of Sapitinib

There total 27 articles about Sapitinib 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: 95.0%

2-[4-(4-amino-5-cyano-2-methoxy-phenoxy)-1-piperidyl]-N-methylacetamide (1196531-38-0) + N,N'-bis(3-chloro-2-fluoro-phenyl)formamidine (1252041-51-2) → Sapitinib (848942-61-0)

Guidance literature:

2-[4-(4-amino-5-cyano-2-methoxy-phenoxy)-1-piperidyl]-N-methylacetamide; N,N'-bis(3-chloro-2-fluoro-phenyl)formamidine; With acetic acid; In 2-methyltetrahydrofuran; at 80 - 92 ℃; for 6h;

With sodium hydroxide; In 2-methyltetrahydrofuran; water; at 55 - 63 ℃; Product distribution / selectivity;

Reference yield: 73.0%

2-[4-(4-amino-5-cyano-2-methoxy-phenoxy)-1-piperidyl]-N-methylacetamide (1196531-38-0) + N'-(3-chloro-2-fluoro-phenyl)-N,N-dimethyl-formamidine (1252041-52-3) → Sapitinib (848942-61-0)

Guidance literature:

2-[4-(4-amino-5-cyano-2-methoxy-phenoxy)-1-piperidyl]-N-methylacetamide; N'-(3-chloro-2-fluoro-phenyl)-N,N-dimethyl-formamidine; With acetic acid; In 2-methyltetrahydrofuran; at 90 ℃; for 14h;

With sodium hydroxide; In 2-methyltetrahydrofuran; water; at 55 - 63 ℃;

Reference yield: 70.0%

N-(3-chloro-2-fluorophenyl)-7-methoxy-6-(piperidin-4-yloxy)quinazolin-4-amine (612500-78-4) + chloroacetylmethylamide (96-30-0) → Sapitinib (848942-61-0)

Guidance literature:

With potassium carbonate; potassium iodide; In acetonitrile; for 2h; Reflux;

DOI:10.1016/j.bmcl.2014.07.092

upstream raw materials:

N-(3-chloro-2-fluorophenyl)-7-methoxy-6-(piperidin-4-yloxy)quinazolin-4-amine

chloroacetylmethylamide

2-[4-(5-cyano-4-{[(dimethylamino)methylene]amino}-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide

3-chloro-2-fluoroaniline

Refernces

• 1、 Wang, Min,Gao, Mingzhang,Zheng, Qi-Huang. "The first radiosynthesis of [11C]AZD8931 as a new potential PET agent for imaging of EGFR, HER2 and HER3 signaling". . p. 4455 - 4459. Retrieved 2014/12/11.
• 2、 -. "PROCESS 738". Page/Page column 17-18; 21. . Retrieved 2010/11/05.