Dasatinib

Base Information

• Chemical Name: Dasatinib
• CAS No.: 863127-77-9
• Molecular Formula: C22H26Cl N7O2S^. H2O
• Molecular Weight: 506.028
• Hs Code.: 29339900
• European Community (EC) Number: 801-607-0,638-874-6
• NSC Number: 759877,732517
• UNII: X78UG0A0RN
• DSSTox Substance ID: DTXSID4040979
• Wikipedia: Dasatinib
• Wikidata: Q419940
• NCI Thesaurus Code: C38713,C74556
• RXCUI: 475342,1546019
• Pharos Ligand ID: WHNTF247H22K
• Metabolomics Workbench ID: 43461
• ChEMBL ID: CHEMBL1421
• Mol file: 863127-77-9.mol

Synonyms:(18F)-N-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide;354825, BMS;BMS 354825;BMS-354825;BMS354825;dasatinib;N-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide;Sprycel

Chemical Property of Dasatinib

Chemical Property:

• Melting Point: 97-99°C(lit.)
• PSA: 143.98000
• Density: 1.408 g/cm3
• LogP: 3.39810
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 487.1557220
• Heavy Atom Count: 33
• Complexity: 642

Purity/Quality:

99.00% ^*data from raw suppliers

DasatinibMonohydrate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CC1=C(C(=CC=C1)Cl)NC(=O)C2=CN=C(S2)NC3=CC(=NC(=N3)C)N4CCN(CC4)CCO
• Recent ClinicalTrials: Serial Measurements of Molecular and Architectural Responses to Therapy (SMMART) PRIME Trial
• Recent EU Clinical Trials: Safety and Impact of Dasatinib on Viral Persistence and Inflammation in People with HIV under Antiretroviral Treatment
• Recent NIPH Clinical Trials: A study of oral asciminib versus other TKIs in adult patients with newly diagnosed Ph+ CML-CP
• Uses: antineoplastic Dasatinib Monohydrate is an orally bioavailable synthetic small molecule-inhibitor of SRC-family protein-tyrosine kinases. It is a COVID19-related research product.

Technology Process of Dasatinib

There total 9 articles about Dasatinib 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: 96.44%

dasatanib (302962-49-8) → dasatinib monohydrate (863127-77-9)

Guidance literature:

With ethanol; water; at 80 ℃; for 2h; Large scale;

Reference yield: 93.0%

N-(2-chloro-6-methylphenyl)-2-((2-methyl-6-(piperazin-1-yl)pyrimidin-4-yl)amino)thiazole-5-carboxamide (910297-51-7) + 2-bromoethanol (540-51-2) → dasatinib monohydrate (863127-77-9)

Guidance literature:

With caesium carbonate; potassium iodide; In acetonitrile; for 6h; Temperature; Solvent; Reagent/catalyst; Reflux;

DOI:10.1080/00397911.2017.1337150

Reference yield: 83.2%

1-(2-hydroxyethyl)piperazine (103-76-4) + 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide (302964-08-5) → dasatinib monohydrate (863127-77-9)

Guidance literature:

1-(2-hydroxyethyl)piperazine; 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide; With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 118 ℃; for 4.5h;

With water; In ethanol;

upstream raw materials:

1-(2-hydroxyethyl)piperazine

2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

dasatanib

N-(2-chloro-6-methylphenyl)-2-((2-methyl-6-(piperazin-1-yl)pyrimidin-4-yl)amino)thiazole-5-carboxamide

Downstream raw materials:

dasatanib

Refernces

• 1、 -. "[...] a novel crystalline form of water composition and its preparation method and pharmaceutical composition". Paragraph 0081-0104. . Retrieved 2018/04/20.
• 2、 -. "POLYMORPHS OF DASATINIB AND PROCESS FOR PREPARATION THEREOF". Page/Page column 32-33. . Retrieved 2009/05/28.