Multi-step reaction with 8 steps
1.1: triphenylphosphine; ozone / methanol; dichloromethane / -78 - 20 °C / Inert atmosphere
2.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene / tert-butyl alcohol; water / 0.5 h
2.2: 2 h
3.1: triethylamine; chloroformic acid ethyl ester; ammonium hydroxide / tetrahydrofuran / 2 h / -20 - -5 °C
4.1: hydrazine / ethanol / 14 h / Reflux
5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / dichloromethane; N,N-dimethyl-formamide / 14 h / -10 - 20 °C
6.1: trifluorormethanesulfonic acid / dichloromethane / 1 h / 0 °C
6.2: 0.5 h / 0 °C
7.1: hydrogen fluoride / dichloromethane / 0.17 h / pH 2 - 3
8.1: sodium hydroxide / dimethylsulfoxide-d6; water-d2 / 0.33 h / 0 - 20 °C
With
4-methyl-morpholine; ammonium hydroxide; sodium dihydrogenphosphate; 2-methyl-but-2-ene; trifluorormethanesulfonic acid; hydrogen fluoride; chloroformic acid ethyl ester; ozone; triethylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; hydrazine;
In
tetrahydrofuran; methanol; dimethylsulfoxide-d6; ethanol; dichloromethane; water; water-d2; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ol301933n