Lapatinib Ditosylate

Base Information

• Chemical Name: Lapatinib Ditosylate
• CAS No.: 388082-77-7
• Molecular Formula: C₇H₈O₃S*C₂₉H₂₆ClFN₄O₄S
• Molecular Weight: 753.272
• Hs Code.: 29420000
• European Community (EC) Number: 642-915-3,879-201-8
• UNII: 4WK72K94MC
• DSSTox Substance ID: DTXSID60959606
• Wikidata: Q27260601
• NCI Thesaurus Code: C66878
• RXCUI: 481474
• ChEMBL ID: CHEMBL1201183
• Mol file: 388082-77-7.mol

Synonyms:GW 282974X;GW 572016;GW-282974X;GW-572016;GW282974X;GW572016;lapatinib;lapatinib ditosylate;N-(3-chloro-4-(((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-methylsulfonyl)ethyl)amino)methyl) -2-furyl)-4-quinazolinamine;Tykerb

Chemical Property of Lapatinib Ditosylate

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 2.03E-22mmHg at 25°C
• Melting Point: 240-242 °C
• Boiling Point: 750.7 °C at 760 mmHg
• Flash Point: 407.8 °C
• PSA: 240.23000
• LogP: 12.32880
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: ≥24.3 mg/mL in DMSO; insoluble in EtOH; insoluble in H2O
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 13
• Exact Mass: 924.1735629
• Heavy Atom Count: 62
• Complexity: 1100

Purity/Quality:

99% ^*data from raw suppliers

LapatinibDitosylate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.CC1=CC=C(C=C1)S(=O)(=O)O.CS(=O)(=O)CCNCC1=CC=C(O1)C2=CC3=C(C=C2)N=CN=C3NC4=CC(=C(C=C4)OCC5=CC(=CC=C5)F)Cl
• Recent ClinicalTrials: Paclitaxel and Trastuzumab With or Without Lapatinib in Treating Patients With Stage II or Stage III Breast Cancer That Can Be Removed by Surgery
• Recent EU Clinical Trials: The ROME trial from histology to target: the road to personalize target therapy and immunotherapy
• Description: Lapatinib, an ErB-1 and ErB-2 dual kinase inhibitor, was launched for the treatment of advanced or metastatic HER2 (ErbB2) positive breast cancer in women who have received prior therapy. The drug was discovered and developed by GlaxoSmithKline and is also currently being evaluated for several additional cancer indications.
• Uses: Reversible dual inhibitor of ErbB1 and ErbB2 tyrosine kinases. Antineoplastic Lapatinib Ditosylate is a reversible dual inhibitor of ErbB1 and ErbB2 tyrosine kinases. Antineoplastic.

Technology Process of Lapatinib Ditosylate

There total 55 articles about Lapatinib Ditosylate 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: 94.9%

2-(methylsulfonyl)ethylamine hydrochloride (104458-24-4) + toluene-4-sulfonic acid (104-15-4) + 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde (231278-84-5) → lapatinib ditosylate (388082-78-8,388082-77-7)

Guidance literature:

2-(methylsulfonyl)ethylamine hydrochloride; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde; With tetrabutylammomium bromide; triethylamine; In tetrahydrofuran; at 30 ℃; for 3h;

With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 20 ℃; for 4h;

toluene-4-sulfonic acid; In tetrahydrofuran; at 50 ℃; for 1h;

Reference yield: 93.0%

2-Methanesulfonyl-ethylamine (49773-20-8) + toluene-4-sulfonic acid (104-15-4) + 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde (231278-84-5) → lapatinib ditosylate (388082-78-8,388082-77-7)

Guidance literature:

2-Methanesulfonyl-ethylamine; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde; In methanol; dichloromethane; at 20 ℃;

With hydrogen; In methanol; dichloromethane; Inert atmosphere;

toluene-4-sulfonic acid; In methanol; dichloromethane;

Reference yield: 92.5%

lapatanib (231277-92-2) + toluene-4-sulfonic acid (104-15-4) → lapatinib ditosylate (388082-78-8,388082-77-7)

Guidance literature:

In tetrahydrofuran; at 20 - 57.5 ℃;

upstream raw materials:

lapatanib

toluene-4-sulfonic acid

2-(methylsulfonyl)ethylamine hydrochloride

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Downstream raw materials:

lapatinib monohydrochloride

lapatinib hydrogen bromide salt

lapatinib citric acid salt

Refernces

• 1、 -. "IMPROVED PROCESS FOR THE PREPARATION OF LAPATINIB BASE AND IT'S ANHYDROUS DITOSYLATE SALT". Paragraph 11. . Retrieved 2020/07/15.
• 2、 -. "Method for synthesizing lapatinib or intermediate thereof". Paragraph 0052; 0053; 0054. . Retrieved 2017/06/30.