Multi-step reaction with 9 steps
1.1: sodium hydroxide / water; ethyl acetate / 0 °C
1.2: 3.5 h / 20 °C
2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 0.08 h / 20 °C / Inert atmosphere
2.2: 24 h / 60 °C
3.1: ammonium formate; 5%-palladium/activated carbon / ethanol / 1 h / 70 °C / Inert atmosphere
4.1: sodium hydrogencarbonate / water; 1,4-dioxane / 20 °C
5.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
6.2: 22 h / 20 °C
7.1: hydrogenchloride; acetic acid; iron / water; ethanol / 2.5 h / Reflux
8.1: 1-methyl-pyrrolidin-2-one / 1 h / 20 °C
9.1: morpholine / tetrahydrofuran; N,N-dimethyl-formamide / 0.25 h / 20 °C
With
morpholine; hydrogenchloride; 5%-palladium/activated carbon; ammonium formate; iron; sodium hydrogencarbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm4004076