N-(5-tert-Butylisoxazol-3-yl)-N'-{4-[7-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea

Base Information

• Chemical Name: N-(5-tert-Butylisoxazol-3-yl)-N'-{4-[7-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea
• CAS No.: 950769-58-1
• Molecular Formula: C₂₉H₃₂N₆O₄S
• Molecular Weight: 560.677
• Hs Code.: 2914500090
• Mol file: 950769-58-1.mol

Synonyms:N-(5-tert-Butylisoxazol-3-yl)-N'-[4-[7-[2-(morpholin-4-yl)ethoxy]imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl]urea;

Chemical Property of N-(5-tert-Butylisoxazol-3-yl)-N'-{4-[7-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea

Chemical Property:

• PKA: 12.59±0.70(Predicted)
• PSA: 134.40000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 5.94040
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to at least 25 mg/ml)

Purity/Quality:

98%, ^*data from raw suppliers

Quizartinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Quizartinib (950769-58-1) is a potent and selective inhibitor of FLT3 (Kd?= 1.6nM, IC50?= 0.56 nM MV4-11 cells).1?It is in clinical trials for treatment of Acute Myelogenous Leukemia (AML).2,3?Quizartinib priming resulted in prevention of myelosuppression in mice treated with 5-FU and Gemcitabine.4?Quizartinib showed significant reversal of ABCG2-mediated multidrug resistance (@ 3 μM)?via?antagonism of drug efflux function.5,6

Technology Process of N-(5-tert-Butylisoxazol-3-yl)-N'-{4-[7-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea

There total 11 articles about N-(5-tert-Butylisoxazol-3-yl)-N'-{4-[7-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea 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: 94.7%

phenyl (5-(tert-butyl)isoxazol-3-yl)carbamate (81479-48-3) + 2-(4-aminophenyl)-7-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazole (950769-61-6) → quizartinib (950769-58-1)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 60 ℃; for 18h; Product distribution / selectivity;

Reference yield: 41.0%

2-(4-aminophenyl)-7-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazole (950769-61-6) + 5-tert-butyl-3-isoxazolyl isocyanate (55809-53-5) → quizartinib (950769-58-1)

Guidance literature:

In toluene; at 120 ℃;

Reference yield: 21.0%

2-(morpholin-4-yl)ethanol (622-40-2) + N-(5-tert-butylisoxazol-3-yl)-N'-[4-(7-hydroxyimidazo[2,1-b][1,3]benzothiazol-2-yl)phenyl]urea (950769-51-4) → quizartinib (950769-58-1)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; Product distribution / selectivity;

upstream raw materials:

2-(4-aminophenyl)-7-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazole

5-tert-butyl-3-isoxazolyl isocyanate

2-(morpholin-4-yl)ethanol

N-(5-tert-butylisoxazol-3-yl)-N'-[4-(7-hydroxyimidazo[2,1-b][1,3]benzothiazol-2-yl)phenyl]urea

Refernces

• 1、 -. "SOLID FORMS COMPRISING N-(5-TERT-BUTYL-ISOXAZOL-3-YL)-N'-{4-[7-(2-MORPHOLIN-4-YL-ETHOXY)IMIDAZO[2,1-B][1,3]BENZOTHIAZOL-2-YL]PHENYL}UREA, COMPOSITIONS THEREOF, AND USES THEREWITH". Page/Page column 85-86. . Retrieved 2009/04/25.
• 2、 -. "Imidazolothiazole compounds for the treatment of disease". Page/Page column 40. . Retrieved 2008/06/13.