Multi-step reaction with 9 steps
1.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
2.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere
3.1: Dess-Martin periodane / dichloromethane / 18 h / 20 °C / Inert atmosphere
4.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane; ethanol / 2.5 h / 20 °C / Inert atmosphere
4.2: 18 h / Inert atmosphere
4.3: Resolution of racemate
5.1: hydrogen; 20% palladium hydroxide-activated charcoal / ethanol / 18 h / 3102.97 Torr / Inert atmosphere
6.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 1 h / 20 °C / Inert atmosphere
7.1: lithium hydroxide / water; tetrahydrofuran; methanol / 0.5 h / 20 °C
8.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
9.1: ammonium acetate / 1,4-dioxane / 100 °C / Sealed tube; Inert atmosphere
With
20% palladium hydroxide-activated charcoal; ammonium acetate; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; acetic acid; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; (bis-(2-methoxyethyl)amino)sulfur trufluoride;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm4013104