Lapatinib ditosylate

Base Information

• Chemical Name: Lapatinib ditosylate
• CAS No.: 388082-78-8
• Molecular Formula: C29H26ClFN4O4S^.2(C7H8O3S)^.H2O
• Molecular Weight: 925.477
• 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: 388082-78-8.mol

Synonyms:GW572016F;Tykerb;UNII-G873GX646R;Lapatinib ditosylate;

Chemical Property of Lapatinib ditosylate

Chemical Property:

• Appearance/Colour: colourless to light-yellow crystal
• Melting Point: 237 - 239 °C
• Boiling Point: 750.7 °C at 760 mmHg
• Flash Point: 407.8 °C
• PSA: 249.46000
• Density: 1.381 g/cm³
• LogP: 12.26450
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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:

99.50% ^*data from raw suppliers

Lapatinib Ditosylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N

MSDS Files:

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
• Uses: anticancer binds to a(1), dopamine, histamine H1, muscarinic, and serotonin type 2 (5-HT2) receptors atypical antipsychotic agent Lapatinib ditosylate monohydrate is a form of Lapatinib I, an orally active drug for breast cancer as a dual EGFR and erbB-?2 inhibitor.

Technology Process of Lapatinib ditosylate

There total 51 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:

lapatanib

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.