Multi-step reaction with 12 steps
1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 °C
2.1: dichloromethane / 1.5 h / 0 - 20 °C
3.1: pyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere
4.1: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 6 h / 20 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C
6.1: hydrogen; palladium 10% on activated carbon / methanol / 4 h
7.1: ethanol / 4 h / 20 °C / Inert atmosphere
8.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere
9.1: sodium tetrahydroborate; ethanol / 1 h / 20 °C
10.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2.5 h / 20 °C
11.1: piperidine / 1,4-dioxane / 1 h / 110 °C / Sealed tube
12.1: trifluoroacetic acid / dichloromethane / 2.5 h / 0 - 20 °C
12.2: 5 °C / pH Ca. 7 - 8
With
piperidine; pyridine; sodium tetrahydroborate; ethanol; palladium 10% on activated carbon; hydrogen; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid;
In
1,4-dioxane; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;