N-(2-methyl-5-(morpholinylmethyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidin-2-yl)amino)benzamide

Base Information

• Chemical Name: N-(2-methyl-5-(morpholinylmethyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidin-2-yl)amino)benzamide
• CAS No.: 1620147-48-9
• Molecular Formula: C₃₂H₂₈F₃N₅O₄
• Molecular Weight: 603.601

Synonyms:N-(2-methyl-5-(morpholinylmethyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidin-2-yl)amino)benzamide

Chemical Property of N-(2-methyl-5-(morpholinylmethyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidin-2-yl)amino)benzamide

Chemical Property:

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Technology Process of N-(2-methyl-5-(morpholinylmethyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidin-2-yl)amino)benzamide

There total 5 articles about N-(2-methyl-5-(morpholinylmethyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidin-2-yl)amino)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: 59.0%

morpholine (110-91-8,99108-56-2) + N-(5-(chloromethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidin-2-yl)amino)benzamide (1620147-44-5) → N-(2-methyl-5-(morpholinylmethyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidin-2-yl)amino)benzamide (1620147-48-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 85 ℃; for 2.5h;

DOI:10.1016/j.bmcl.2014.05.066

Reference yield:

2,4-dichloro-furo[3,2-d]pyrimidine (956034-07-4) → N-(2-methyl-5-(morpholinylmethyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidin-2-yl)amino)benzamide (1620147-48-9)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 4 h / 80 °C

2: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / 1,4-dioxane / 4 h / 150 °C / Microwave irradiation

3: sodium hydroxide; water / methanol / Reflux

4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 80 °C

5: thionyl chloride / dichloromethane / 2.5 h / 20 °C

6: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 85 °C

With bis-triphenylphosphine-palladium(II) chloride; thionyl chloride; water; palladium diacetate; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2014.05.066

Reference yield:

2-chloro-4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidine (1620147-32-1) → N-(2-methyl-5-(morpholinylmethyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidin-2-yl)amino)benzamide (1620147-48-9)

Guidance literature:

Multi-step reaction with 5 steps

1: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / 1,4-dioxane / 4 h / 150 °C / Microwave irradiation

2: sodium hydroxide; water / methanol / Reflux

3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 80 °C

4: thionyl chloride / dichloromethane / 2.5 h / 20 °C

5: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 85 °C

With thionyl chloride; water; palladium diacetate; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2014.05.066

upstream raw materials:

2,4-dichloro-furo[3,2-d]pyrimidine

2-chloro-4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidine

N-(5-(hydroxymethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)furo[3,2-d]pyrimidin-2-yl)amino)benzamide

morpholine

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