Multi-step reaction with 12 steps
1.1: thionyl chloride / 16 h / 0 - 20 °C
2.1: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C
3.1: tetrahydrofuran; diethyl ether / 2 h / 0 °C / Inert atmosphere
4.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
5.1: hydrogen; palladium 10% on activated carbon / ethanol / 16 h
6.1: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C
7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -20 °C
7.2: 3 h / 20 °C
8.1: sodium hydroxide / water; tetrahydrofuran; ethanol / 4 h / 90 °C
9.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 20 °C
10.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 16 h / 20 °C
11.1: hydrogen; palladium 10% on activated carbon / methanol / 16 h / 20 °C
12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 20 °C
With
dmap; thionyl chloride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water;