Technology Process of 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
There total 8 articles about 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 which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate; 1,1'-Thiocarbonyldi-2(1H)-pyridone;
In
dichloromethane;
at 20 ℃;
for 0.5h;
cyclobutanecarboxylic acid hydrazide;
In
dichloromethane;
at 20 ℃;
for 1h;
With
1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
In
dichloromethane;
at 20 ℃;
for 1h;
DOI:10.1021/acsmedchemlett.9b00117
- Guidance literature:
-
In
dichloromethane;
at 20 ℃;
for 1h;
In
dichloromethane;
at 20 ℃;
for 1h;
With
N-(3-dimethylaminopropyl)-N-ethylcarbodiimide;
In
dichloromethane;
at 20 ℃;
- Guidance literature:
-
Multi-step reaction with 7 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
With
tetrakis(triphenylphosphine) palladium(0); potassium acetate; sodium hydride; diisobutylaluminium hydride; sodium carbonate; toluene-4-sulfonic acid;
In
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
