Fedratinib

Base Information

• Chemical Name: Fedratinib
• CAS No.: 936091-26-8
• Molecular Formula: C₂₇H₃₆N₆O₃S
• Molecular Weight: 524.687
• Hs Code.: 29350090
• European Community (EC) Number: 829-304-9
• UNII: 6L1XP550I6
• ChEMBL ID: CHEMBL1287853
• DSSTox Substance ID: DTXSID90239483
• Metabolomics Workbench ID: 153478
• NCI Thesaurus Code: C88293
• Nikkaji Number: J2.685.244G
• Pharos Ligand ID: GUJY5FTRMBSB
• RXCUI: 2197490
• Wikidata: Q7670147
• Wikipedia: Fedratinib
• Mol file: 936091-26-8.mol

Synonyms:Fedratinib;fedratinib dihydrochloride monohydrate;fedratinib hydrochloride;fedratinib hydrochloride monohydrate;Inrebic;N-tert-butyl-3-((5-methyl-2-((4-(2-pyrrolidin-1-ylethoxy)phenyl)amino)pyrimidin-4-yl)amino) benzenesulfonamide dihydrochloride monohydrate;N-tert-butyl-3-(5-methyl-2-(4-(2-(pyrrolidin-1-yl)ethoxy)phenylamino) pyrimidin-4-ylamino)benzenesulfonamide;SAR-302503;SAR-302503A;SAR302503;SAR302503A;TG-101348;TG101348

Chemical Property of Fedratinib

Chemical Property:

• Boiling Point: 713.7 °C at 760 mmHg
• PKA: 11.95±0.50(Predicted)
• Flash Point: 385.5 °C
• PSA: 120.09000
• Density: 1.247g/cm³
• LogP: 5.72810
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 524.25696021
• Heavy Atom Count: 37
• Complexity: 787

Purity/Quality:

99% ^*data from raw suppliers

TG101348 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents, Tyrosine Kinase Inhibitor
• Canonical SMILES: CC1=CN=C(N=C1NC2=CC(=CC=C2)S(=O)(=O)NC(C)(C)C)NC3=CC=C(C=C3)OCCN4CCCC4
• Recent ClinicalTrials: Decitabine With Ruxolitinib, Fedratinib or Pacritinib for the Treatment of Accelerated/Blast Phase Myeloproliferative Neoplasms
• Description: Fedratinib (SAR302503, TG101348) is a selective inhibitor of JAK2 with IC50 of 3 nM in cell-free assays, 35-and 334-fold more selective for JAK2 versus JAK1 and JAK3. Phase 2.
• Uses: TG101348 is a selective inhibitor of JAK2 tyrosine kinase. Potent JAK2 inhibitor.

Technology Process of Fedratinib

There total 10 articles about Fedratinib 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: 93.0%

3-((5-methyl-2-((4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)amino)pyrimidin-4-yl)amino)benzenesulfonyl fluoride + tert-butylamine (75-64-9) → N-tert-butyl-3-{5-methyl-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-pyrimidin-4-ylamino}-benzenesulfonamide (936091-26-8)

Guidance literature:

With 1,1,3,3-Tetramethyldisiloxane; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 25 ℃; for 24h; Reagent/catalyst; Temperature;

Reference yield: 83.0%

N-(tert-butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide (936092-53-4) + 4-(2-pyrrolidinoethoxy)aniline (50609-01-3) → N-tert-butyl-3-{5-methyl-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-pyrimidin-4-ylamino}-benzenesulfonamide (936091-26-8)

Guidance literature:

With potassium carbonate; at 65 ℃; for 12h;

DOI:10.1016/j.mcat.2021.112011

Reference yield:

3-bromo-(N-tert-butyl)benzenesulfonamide (308283-47-8) + 2-chloro-4-amino-5-methylpyrimidine (14394-70-8) → N-tert-butyl-3-{5-methyl-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-pyrimidin-4-ylamino}-benzenesulfonamide (936091-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 3 h / Inert atmosphere; Reflux

2: acetic acid / 0.33 h / 150 °C / Microwave irradiation; Sealed tube

With caesium carbonate; acetic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane;

upstream raw materials:

N-(tert-butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide

4-(2-pyrrolidinoethoxy)aniline

3-bromo-(N-tert-butyl)benzenesulfonamide

2-chloro-4-amino-5-methylpyrimidine

Refernces

• 1、 Hajipour, Abdol R.,Khorsandi, Zahra,Sarfjoo, Mohamad Reza,Varma, Rajender S.. "A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib". supporting information. p. 5222 - 5229. Retrieved 2021/07/29.
• 2、 -. "Sulfonyl fluoride compound, preparation method thereof and method for preparing sulfonamide compound through sulfonyl fluoride compound". . . Retrieved 2020/12/31.