4-((5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)-N-(2-methyl-5-((1-methylhexahydropyrrole[3,4-b]pyrrolidin-5(1H)-yl)methyl)phenyl)benzamide

Base Information

• Chemical Name: 4-((5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)-N-(2-methyl-5-((1-methylhexahydropyrrole[3,4-b]pyrrolidin-5(1H)-yl)methyl)phenyl)benzamide
• CAS No.: 1550175-21-7
• Molecular Formula: C₃₄H₃₅F₃N₆O₂
• Molecular Weight: 616.686
• Mol file: 1550175-21-7.mol

Synonyms:

Chemical Property of 4-((5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)-N-(2-methyl-5-((1-methylhexahydropyrrole[3,4-b]pyrrolidin-5(1H)-yl)methyl)phenyl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)-N-(2-methyl-5-((1-methylhexahydropyrrole[3,4-b]pyrrolidin-5(1H)-yl)methyl)phenyl)benzamide

There total 8 articles about 4-((5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)-N-(2-methyl-5-((1-methylhexahydropyrrole[3,4-b]pyrrolidin-5(1H)-yl)methyl)phenyl)benzamide 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: 40.0%

→ 4-((5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)-N-(2-methyl-5-((1-methylhexahydropyrrole[3,4-b]pyrrolidin-5(1H)-yl)methyl)phenyl)benzamide (1550175-21-7)

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

N-(5-(chloromethyl)-2-methylphenyl)-4-((5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)benzamide + 2-Methyl-2,7-diazabicyclo[3.3.0]octane (128740-09-0) → 4-((5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)-N-(2-methyl-5-((1-methylhexahydropyrrole[3,4-b]pyrrolidin-5(1H)-yl)methyl)phenyl)benzamide (1550175-21-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmcl.2013.12.050

Reference yield:

2,6-dichloro-5-methylpyrimidine (1780-31-0) → 4-((5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)-N-(2-methyl-5-((1-methylhexahydropyrrole[3,4-b]pyrrolidin-5(1H)-yl)methyl)phenyl)benzamide (1550175-21-7)

Guidance literature:

Multi-step reaction with 6 steps

1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide; water / 80 °C

2: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / 1,4-dioxane / 3 h / 170 °C / Microwave irradiation

3: sodium hydroxide; water / methanol / Reflux

4: 2-( 1H-7-azabenzotniazol-1-yl)-1,1,3,3-tetrarmethyluroniumhexafluorophosphate methanaminium; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 85 °C

5: thionyl chloride / dichloromethane / 2 h / 20 °C

6: potassium carbonate / N,N-dimethyl-formamide / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; thionyl chloride; 2-( 1H-7-azabenzotniazol-1-yl)-1,1,3,3-tetrarmethyluroniumhexafluorophosphate methanaminium; water; palladium diacetate; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: |Suzuki Coupling / 2: |Buchwald-Hartwig Coupling;

DOI:10.1016/j.bmcl.2013.12.050

upstream raw materials:

2-Methyl-2,7-diazabicyclo[3.3.0]octane

2,6-dichloro-5-methylpyrimidine

4-trifluoromethoxyphenylboronic acid

Refernces

• 1、 Xin, Minhang,Wen, Jun,Tang, Feng,Tu, Chongxing,Huang, Wei,Shen, Han,Zhao, Xinge,Cheng, Lingfei,Wang, Mengyu,Zhang, Liandi. "Synthesis and evaluation of 4-(2-pyrimidinylamino) benzamides inhibitors of hedgehog signaling pathway". . p. 983 - 988. Retrieved 2014/02/14.