2-[4-(3-{(R)-1-cyclopropyl-1-[4-(2-isopropylamino-pyrimidin-5-yl)-phenyl]-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-N,N-dimethyl-acetamide

Base Information

• Chemical Name: 2-[4-(3-{(R)-1-cyclopropyl-1-[4-(2-isopropylamino-pyrimidin-5-yl)-phenyl]-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-N,N-dimethyl-acetamide
• CAS No.: 1360551-67-2
• Molecular Formula: C₂₇H₃₂N₈O₂
• Molecular Weight: 500.603
• Mol file: 1360551-67-2.mol

Synonyms:

Chemical Property of 2-[4-(3-{(R)-1-cyclopropyl-1-[4-(2-isopropylamino-pyrimidin-5-yl)-phenyl]-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-N,N-dimethyl-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[4-(3-{(R)-1-cyclopropyl-1-[4-(2-isopropylamino-pyrimidin-5-yl)-phenyl]-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-N,N-dimethyl-acetamide

There total 8 articles about 2-[4-(3-{(R)-1-cyclopropyl-1-[4-(2-isopropylamino-pyrimidin-5-yl)-phenyl]-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-N,N-dimethyl-acetamide 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: 44.0%

(5-bromopyrimidin-2-yl)-N-isopropylamine (77476-95-0) + 2-[4-(3-{(R)-1-cyclopropyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]ethyl}-[1,2,4]oxadiazol-5-yl)pyrazol-1-yl]-N,N-dimethylacetamide (1360552-43-7) → 2-[4-(3-{(R)-1-cyclopropyl-1-[4-(2-isopropylamino-pyrimidin-5-yl)-phenyl]-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-N,N-dimethyl-acetamide (1360551-67-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 0.333333h; Inert atmosphere; Microwave irradiation; Sealed tube;

DOI:10.1021/jm501185j

Reference yield:

(R)-2-(4-bromophenyl)-2-cyclopropyl-N′-hydroxypropanimidamide (1360551-95-6) → 2-[4-(3-{(R)-1-cyclopropyl-1-[4-(2-isopropylamino-pyrimidin-5-yl)-phenyl]-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-N,N-dimethyl-acetamide (1360551-67-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1,1'-carbonyldiimidazole / 1-methyl-pyrrolidin-2-one / 0.5 h / 50 °C / Inert atmosphere

1.2: 16 h / 100 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere; Sealed tube

4.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / N,N-dimethyl-formamide / 0.33 h / 90 °C / Inert atmosphere; Microwave irradiation; Sealed tube

With bis-triphenylphosphine-palladium(II) chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium carbonate; potassium carbonate; 1,1'-carbonyldiimidazole; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; 3.1: |Suzuki-Miyaura Coupling / 4.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm501185j

Reference yield:

C11H10BrN → 2-[4-(3-{(R)-1-cyclopropyl-1-[4-(2-isopropylamino-pyrimidin-5-yl)-phenyl]-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-N,N-dimethyl-acetamide (1360551-67-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C / Inert atmosphere

1.2: methyl halide / 16 h / Inert atmosphere; Heating

2.1: carbon dioxide / ethanol / 38 °C / 75007.5 Torr / Resolution of racemate

3.1: hydroxylamine / ethanol; water / 16 h / 80 °C / Inert atmosphere

4.1: 1,1'-carbonyldiimidazole / 1-methyl-pyrrolidin-2-one / 0.5 h / 50 °C / Inert atmosphere

4.2: 16 h / 100 °C / Inert atmosphere

5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

6.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere; Sealed tube

7.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / N,N-dimethyl-formamide / 0.33 h / 90 °C / Inert atmosphere; Microwave irradiation; Sealed tube

With bis-triphenylphosphine-palladium(II) chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; carbon dioxide; hydroxylamine; potassium acetate; sodium hydride; sodium carbonate; potassium carbonate; 1,1'-carbonyldiimidazole; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; ethanol; water; N,N-dimethyl-formamide; mineral oil; 6.1: |Suzuki-Miyaura Coupling / 7.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm501185j

upstream raw materials:

(R)-2-(4-bromophenyl)-2-cyclopropyl-N′-hydroxypropanimidamide

(5-bromopyrimidin-2-yl)-N-isopropylamine

2-[4-(3-{(R)-1-cyclopropyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]ethyl}-[1,2,4]oxadiazol-5-yl)pyrazol-1-yl]-N,N-dimethylacetamide

2-(4-bromo-phenyl)-2-cyclopropylpropionitrile

Refernces

• 1、 -. "OXADIAZOLE INHIBITORS OF LEUKOTRIENE PRODUCTION FOR COMBINATION THERAPY". Paragraph 0504; 0505; 0506; 0522; 0600. . Retrieved 2013/08/14.