Multi-step reaction with 9 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 4 h / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
3.1: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 760.05 Torr / Inert atmosphere
4.1: 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 / 0.33 h / 0 °C / Inert atmosphere
4.2: 0 - 20 °C / Inert atmosphere
5.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
6.1: 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 / 0.33 h / 0 °C / Inert atmosphere
6.2: 0 - 20 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
8.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
9.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere
With
oxalyl dichloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tetlet.2012.12.111