Tak-285

Base Information

• Chemical Name: Tak-285
• CAS No.: 871026-44-7
• Molecular Formula: C26H25ClF3N5O3
• Molecular Weight: 547.96
• UNII: 70CCB438L6
• ChEMBL ID: CHEMBL1614725
• DSSTox Substance ID: DTXSID10236136
• NCI Thesaurus Code: C90589
• Nikkaji Number: J3.144.756I
• Wikidata: Q27265858
• Mol file: 871026-44-7.mol

Synonyms:N-(2-(4-((3-chloro-4-(3-(trifluoromethyl)phenoxy)phenyl)amino)-5H-pyrrolo(3,2-d)pyrimidin-5-yl)ethyl)-3-hydroxy-3-methylbutanamide;TAK 285;TAK-285;TAK285

Chemical Property of Tak-285

Chemical Property:

• Melting Point: 167-169℃
• Boiling Point: 705.5±60.0 °C(Predicted)
• PKA: 14.56±0.29(Predicted)
• PSA: 104.79000
• Density: 1.39
• LogP: 6.82990
• Solubility.: ≥27.4 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 547.1598019
• Heavy Atom Count: 38
• Complexity: 792

Purity/Quality:

97% ^*data from raw suppliers

N-(2-(4-(3-Chloro-4-(3-(trifluoromethyl)phenoxy)phenylamino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl)-3-hydroxy-3-methylbutanamide 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(CC(=O)NCCN1C=CC2=C1C(=NC=N2)NC3=CC(=C(C=C3)OC4=CC=CC(=C4)C(F)(F)F)Cl)O
• Uses: TAK-285 is a novel dual HER2 and EGFR inhibitor with IC50 of 17 nM and 23 nM, respectively.

Technology Process of Tak-285

There total 8 articles about Tak-285 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: 77.0%

5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride + 3-Hydroxy-3-methylbutyric acid (625-08-1) → TAK-285 (871026-44-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 72h;

DOI:10.1021/jm2008634

Reference yield:

tert-butyl [2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl]carbamate (871026-37-8) → TAK-285 (871026-44-7)

Guidance literature:

Multi-step reaction with 3 steps

1: isopropyl alcohol / 12 h / 80 °C

2: hydrogenchloride / tetrahydrofuran; water / 20 h / 60 °C

3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm2008634

Reference yield:

tert-butyl {2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}carbamate → TAK-285 (871026-44-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / tetrahydrofuran; water / 20 h / 60 °C

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/jm2008634

upstream raw materials:

3-Hydroxy-3-methylbutyric acid

tert-butyl [2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl]carbamate

3-chloro-4-fluoronitrobenzene

3-Trifluoromethylphenol