AUZ 454

Base Information

• Chemical Name: AUZ 454
• CAS No.: 853299-07-7
• Molecular Formula: C24H26F3N7O2
• Molecular Weight: 501.50400
• Mol file: 853299-07-7.mol

Synonyms:1-[4-(2-amino-pyrimidin-4-yloxy)-phenyl]-3-[4-(4-methyl-piperazin-1-ylmethyl)-3-rifluoromethyl-phenyl]-urea;1-[4-(2-aminopyrimidine-4-yloxy)phenyl]-3-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]urea;

Chemical Property of AUZ 454

Chemical Property:

• PSA: 108.64000
• LogP: 4.86430
• Solubility.: ≥50.2 mg/mL in DMSO; insoluble in H2O; ≥45.4 mg/mL in EtOH

Purity/Quality:

99% ^*data from raw suppliers

K03861 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of AUZ 454

There total 11 articles about AUZ 454 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: 91.0%

[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-carbamic acid phenyl ester hydrochloride + 4-(4-aminophenoxy)pyrimidin-2-ylamine dihydrochloride salt → 1-[4-(2-aminopyrimidine-4-yloxy)phenyl]-3-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]urea (853299-07-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60 - 65 ℃; for 2h; Large scale;

DOI:10.1021/op800136f

Reference yield:

4-amino-2-trifluoromethylbenzonitrile (654-70-6) → 1-[4-(2-aminopyrimidine-4-yloxy)phenyl]-3-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]urea (853299-07-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.08 h / Inert atmosphere; Large scale

2.1: hydrogenchloride / toluene; ethyl acetate; water / 0.08 h / 20 - 25 °C

2.2: 76 - 78 °C

3.1: triethylamine; bis(trichloromethyl) carbonate / dimethyl sulfoxide; dichloromethane

With hydrogenchloride; bis(trichloromethyl) carbonate; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1021/op800136f

Reference yield:

2-chloro-4-(4-nitro-phenoxy)-pyrimidine → 1-[4-(2-aminopyrimidine-4-yloxy)phenyl]-3-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]urea (853299-07-7)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonium hydroxide

2: hydrogen

3: triethylamine; bis(trichloromethyl) carbonate / dimethyl sulfoxide; dichloromethane

With ammonium hydroxide; bis(trichloromethyl) carbonate; hydrogen; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1021/op800136f

upstream raw materials:

4-amino-2-trifluoromethylbenzonitrile

4-amino-2-(trifluoromethyl)benzaldehyde

4-N-tert-butoxycarbonylaminophenol

4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethylaniline

Downstream raw materials:

1-[4-(2-acetylamino-pyrimidin-4-yloxy)-phenyl]-3-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-urea

Refernces

• 1、 -. "DIARYL UREA DERIVATIVES IN THE TREATMENT OF PROTEIN KINASE DEPENDENT DISEASES". Page/Page column 101. . Retrieved 2008/06/13.