Multi-step reaction with 7 steps
1.1: pyridinium p-toluenesulfonate; magnesium sulfate / dichloromethane / 40 °C
2.1: dichloromethane; diethyl ether / 22 h / -50 - 20 °C
3.1: hydrogenchloride / water; methanol / 20 °C
4.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 0.08 h
4.2: 0.5 h / 20 °C
5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C
6.1: hydrazine hydrochloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 16 h / 20 °C
7.1: sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 - 50 °C
With
hydrogenchloride; hydrazine hydrochloride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; magnesium sulfate; 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
methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/acsmedchemlett.5b00218