Barasertib

Base Information

• Chemical Name: Barasertib
• CAS No.: 722543-31-9
• Deprecated CAS: 936487-68-2,957881-03-7
• Molecular Formula: C₂₆H₃₁FN₇O₆P
• Molecular Weight: 587.548
• UNII: 16XC2U7W8N
• ChEMBL ID: CHEMBL415049
• DSSTox Substance ID: DTXSID00222583
• Metabolomics Workbench ID: 152852
• NCI Thesaurus Code: C62502
• Nikkaji Number: J2.604.274G,J2.770.487E
• Pharos Ligand ID: VYAUT369LXAA,XU9G7YAMBB2P
• Wikidata: Q27074865
• Mol file: 722543-31-9.mol

Synonyms:2-((3-((4-((5-(2-((3-fluorophenyl)amino)-2-oxoethyl)-1H-pyrazol-3-yl)amino)quinazolin-7-yl)oxy)propyl)(ethyl)amino)ethyl dihydrogen phosphate;AZD 1152;AZD-1152;AZD1152;barasertib

Chemical Property of Barasertib

Chemical Property:

• PKA: 1.75±0.10(Predicted)
• PSA: 184.63000
• Density: 1.463
• LogP: 3.76290
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥5.88 mg/mL in DMSO
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 15
• Exact Mass: 587.20574689
• Heavy Atom Count: 41
• Complexity: 859

Purity/Quality:

98% min ^*data from raw suppliers

Barasertib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CCCOC1=CC2=C(C=C1)C(=NC=N2)NC3=NNC(=C3)CC(=O)NC4=CC(=CC=C4)F)CCOP(=O)(O)O
• Recent ClinicalTrials: Study to Investigate the Efficacy, Safety and Tolerability of AZD1152 Alone and in Combination With Low Dose Cytosine Arabinoside (LDAC)in Acute Myeloid Leukaemia (AML) Patients
• Recent EU Clinical Trials: A phase 2 trial of AZD1152 in relapsed/refractory diffuse large B-cell lymphoma

Technology Process of Barasertib

There total 12 articles about Barasertib 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: 81.0%

mono(tert-butyl) 2-[[3-([4-[(5-[2-[(3-fluorophenyl)amino]-2-oxoethyl]-1H-pyrazol-3-yl)amino]-quinazolin-7-yl]oxy)propyl](ethyl)amino]ethyl phosphate → 2-{ethyl[3-({4-[(5-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazol-3-yl)amino]quinazolin-7-yl}oxy)proplyl]amino}ethyl dihydrogen phosphate (957881-03-7,722543-31-9)

Guidance literature:

mono(tert-butyl) 2-[[3-([4-[(5-[2-[(3-fluorophenyl)amino]-2-oxoethyl]-1H-pyrazol-3-yl)amino]-quinazolin-7-yl]oxy)propyl](ethyl)amino]ethyl phosphate; With hydrogenchloride; water; In tetrahydrofuran; at 55 - 65 ℃; for 1h;

With sodium hydroxide; water; In tetrahydrofuran; at 55 - 65 ℃; for 1h; pH=5.0 - 5.5;

Reference yield: 73.0%

Barasertib dihydrochloride → 2-{ethyl[3-({4-[(5-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazol-3-yl)amino]quinazolin-7-yl}oxy)proplyl]amino}ethyl dihydrogen phosphate (957881-03-7,722543-31-9)

Guidance literature:

With cyclohexane-1,2-epoxide; In methanol; at 20 ℃;

DOI:10.1021/jm061335f

Reference yield:

2-(5-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-2H-pyrazol-3-yl)-N-(3-fluorophenyl)acetamide (722544-46-9) → 2-{ethyl[3-({4-[(5-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazol-3-yl)amino]quinazolin-7-yl}oxy)proplyl]amino}ethyl dihydrogen phosphate (957881-03-7,722543-31-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 59 percent / potassium iodide / N,N-dimethyl-acetamide / 50 °C

2.1: tetrazole / dimethylformamide / 20 °C

2.2: 63 percent / aq. hydrogen peroxide / dimethylformamide / 2 h / 20 °C

3.1: 99 percent / HCl / dioxane / 20 - 45 °C

4.1: 73 percent / cyclohexene oxide / methanol / 20 °C

With 1H-tetrazole; hydrogenchloride; cyclohexane-1,2-epoxide; potassium iodide; In 1,4-dioxane; methanol; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1021/jm061335f

upstream raw materials:

2-(5-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-2H-pyrazol-3-yl)-N-(3-fluorophenyl)acetamide

(5-amino-2H-pyrazol-3-yl)acetic acid

N-(3-fluorophenyl)-2-{3-[(7-{3-[ethyl(2-hydroxyethyl)amino]propoxy}quinazolin-4-yl)amino]-1H-pyrazol-5-yl}acetamide

di-tert-butyl 2-[[3-({4-[(5-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazol-3-yl)amino]quinazolin-7-yl}oxy)propyl](ethyl)amino]ethyl phosphate

Refernces

• 1、 -. "MALEATE CO-CRYSTAL OF AZD1152". Page/Page column 27-28; 32. . Retrieved 2008/06/13.
• 2、 Mortlock, Andrew A.,Foote, Kevin M.,Heron, Nicola M.,Jung, Frédéric H.,Pasquet, Georges,Lohmann, Jean-Jacques M.,Warin, Nicolas,Renaud, Fabrice,De Savi, Chris,Roberts, Nicola J.,Johnson, Trevor,Dousson, Cyril B.,Hill, George B.,Perkins, David,Hatter, Glenn,Wilkinson, Robert W.,Wedge, Stephen R.,Heaton, Simon P.,Odedra, Rajesh,Keen, Nicholas J.,Crafter, Claire,Brown, Elaine,Thompson, Katherine,Brightwell, Stephen,Khatri, Liz,Brady, Madeleine C.,Kearney, Sarah,McKillop, David,Rhead, Steve,Parry, Tony,Green, Stephen. "Discovery, synthesis, and in vivo activity of a new class of pyrazoloquinazolines as selective inhibitors of aurora B kinase". . p. 2213 - 2224. Retrieved 2008/02/02.