Multi-step reaction with 13 steps
1.1: hydrogen / palladium 10% on activated carbon / 2585.81 Torr
2.1: triethylamine / dichloromethane / 0.5 h / -20 °C
3.1: ethanol; water / 20 - 60 °C
4.1: hydrogenchloride; water / 0 °C / Reflux
5.1: thionyl chloride / 0 °C / Reflux
6.1: triethylamine / dichloromethane / 0 - 20 °C
7.1: potassium tert-butylate / tetrahydrofuran / 20 °C / Cooling with ice
8.1: hydrogenchloride; water / 0 °C / Reflux
9.1: triethylamine / dichloromethane / 20 °C
10.1: acetic acid / methanol / 0 °C
10.2: 0 °C
11.1: tetrahydrofuran / 25 °C / Inert atmosphere; Cooling with ice
12.1: dichloromethane / 0 - 23 °C
13.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 0 °C
With
hydrogenchloride; thionyl chloride; potassium tert-butylate; water; hydrogen; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; HATU;
palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water;