Technology Process of N-{4-[(3S)-3-aminopiperidin-1-yl]-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl}-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide
There total 11 articles about N-{4-[(3S)-3-aminopiperidin-1-yl]-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl}-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
trifluoroacetic acid;
In
dichloromethane;
at 20 - 30 ℃;
for 1h;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C
1.2: 0.5 h / -78 °C
2.1: ammonium acetate; potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3.1: sulfuric acid; nitric acid / 0.5 h / 0 - 30 °C
4.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 14 h / 140 °C
5.1: dmap / acetonitrile / 2 h / 20 - 30 °C
6.1: iron; acetic acid / water / 2 h / 20 - 30 °C
7.1: 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 / 2 h / 50 °C
8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 - 30 °C
With
dmap; sulfuric acid; ammonium acetate; nitric acid; iron; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium iodide; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; butan-1-ol;
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: bis(tri-t-butylphosphine)palladium(0); N-ethyl-N,N-diisopropylamine / water; 1,4-dioxane / 2 h / 100 °C / Sealed tube; Inert atmosphere
2.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 3 h / 50 °C
2.2: 0 °C / pH 2
3.1: 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 / 2 h / 50 °C
4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 - 30 °C
With
bis(tri-t-butylphosphine)palladium(0); lithium hydroxide monohydrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
