2-(4-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

Base Information

• Chemical Name: 2-(4-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid
• CAS No.: 1477523-82-2
• Molecular Formula: C₂₆H₂₈N₄O₄
• Molecular Weight: 460.533

Synonyms:2-(4-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

Chemical Property of 2-(4-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

Chemical Property:

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Technology Process of 2-(4-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

There total 8 articles about 2-(4-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid 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: 41.0%

methyl 2-(4-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (1477524-12-1) → 2-(4-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid (1477523-82-2)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 7h;

Reference yield:

methyl 8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate (1477524-04-1) → 2-(4-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid (1477523-82-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C

2.1: toluene-4-sulfonic acid / water; acetone / 1 h / 75 °C

3.1: sodium hydride / mineral oil; methanol / 0.5 h / 20 °C

3.2: 18 h / 20 °C

4.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / 20 - 100 °C / Cooling with ice

5.1: potassium acetate / 1,4-dioxane / 0.25 h / 20 °C / Inert atmosphere

5.2: 18 h / 80 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 0.83 h / 120 °C / Microwave irradiation

7.1: dichloromethane / 0.5 h / 20 °C

7.2: 1 h / 20 °C

7.3: 1 h / 20 °C

8.1: sodium hydroxide; water / tetrahydrofuran / 7 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; potassium acetate; sodium hydride; diisobutylaluminium hydride; sodium carbonate; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetone; toluene; mineral oil; 3.1: |Horner-Wadsworth-Emmons Olefination / 3.2: |Horner-Wadsworth-Emmons Olefination / 4.1: |Michael Addition;

DOI:10.1021/acsmedchemlett.9b00117

Reference yield:

(8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol (1477524-05-2) → 2-(4-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid (1477523-82-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: toluene-4-sulfonic acid / water; acetone / 1 h / 75 °C

2.1: sodium hydride / mineral oil; methanol / 0.5 h / 20 °C

2.2: 18 h / 20 °C

3.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / 20 - 100 °C / Cooling with ice

4.1: potassium acetate / 1,4-dioxane / 0.25 h / 20 °C / Inert atmosphere

4.2: 18 h / 80 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 0.83 h / 120 °C / Microwave irradiation

6.1: dichloromethane / 0.5 h / 20 °C

6.2: 1 h / 20 °C

6.3: 1 h / 20 °C

7.1: sodium hydroxide; water / tetrahydrofuran / 7 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; potassium acetate; sodium hydride; sodium carbonate; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetone; mineral oil; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination / 3.1: |Michael Addition;

DOI:10.1021/acsmedchemlett.9b00117

upstream raw materials:

methyl 8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate

(8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol

methyl 2-(4-(4-bromophenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

methyl 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

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