Multi-step reaction with 10 steps
1.1: palladium 10% on activated carbon; ammonium formate / methanol / 14 h / 20 °C
2.1: sodium hydrogencarbonate / water; 1,4-dioxane / 14 h / 0 - 20 °C
3.1: 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / dichloromethane
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.17 h
5.1: triethylamine / dichloromethane / 14 h
6.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C / Inert atmosphere
7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere
7.2: 2 h / 0 - 20 °C / Inert atmosphere
8.1: trifluoroacetic acid; water / dichloromethane / 0.5 h / 20 °C
9.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C
10.1: trifluoroacetic acid / dichloromethane / 0.5 h
With
lithium aluminium tetrahydride; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); palladium 10% on activated carbon; water; ammonium formate; sodium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jm3016987