Technology Process of (R)-7-(2,6-difluorophenyl)-6-((3R,4R)-1,3-dimethylpiperidin-4-yl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triazaphenanthren-3-one
There total 12 articles about (R)-7-(2,6-difluorophenyl)-6-((3R,4R)-1,3-dimethylpiperidin-4-yl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triazaphenanthren-3-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
formaldehyd; C23H24F2N4O2;
With
acetic acid;
In
methanol;
at 20 ℃;
for 1h;
With
sodium cyanoborohydride;
In
methanol;
DOI:10.1021/jm5013006
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / 0 °C
1.2: 2 h / 20 °C
2.1: Lawessons reagent / toluene / 3 h / 120 °C
3.1: hydrazine hydrate / ethanol / 20 °C
4.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 4 h / 90 °C
5.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 80 °C
5.2: chiralpak AD
6.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / 760.05 Torr
7.1: tetra-N-butylammonium tribromide / methanol; dichloromethane / 0.5 h / 20 °C
8.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 16 h / 90 °C
9.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 90 °C
10.1: hydrogenchloride / ethyl acetate / 1 h / 20 °C
11.1: acetic acid / methanol / 1 h / 20 °C
With
Lawessons reagent; hydrogenchloride; potassium phosphate; tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium 10% on activated carbon; hydrogen; potassium acetate; tetra-N-butylammonium tribromide; potassium hexamethylsilazane; sodium carbonate; hydrazine hydrate; acetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
5.1: |Suzuki Coupling;
DOI:10.1021/jm5013006
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: Lawessons reagent / toluene / 3 h / 120 °C
2.1: hydrazine hydrate / ethanol / 20 °C
3.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 4 h / 90 °C
4.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 80 °C
4.2: chiralpak AD
5.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / 760.05 Torr
6.1: tetra-N-butylammonium tribromide / methanol; dichloromethane / 0.5 h / 20 °C
7.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 16 h / 90 °C
8.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 90 °C
9.1: hydrogenchloride / ethyl acetate / 1 h / 20 °C
10.1: acetic acid / methanol / 1 h / 20 °C
With
Lawessons reagent; hydrogenchloride; potassium phosphate; tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium 10% on activated carbon; hydrogen; potassium acetate; tetra-N-butylammonium tribromide; sodium carbonate; hydrazine hydrate; acetic acid;
In
1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
4.1: |Suzuki Coupling;
DOI:10.1021/jm5013006