N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate in N,N-dimethyl-formamide T=20°C; 18 h;

1: SOCl2; DMAP / toluene / 1 h / Heating 2: 13.3 g / NH3(g) / CH2Cl2 / 20 °C 3: 94 percent / pyridine; TFAA / dioxane / 3 h / 20 °C 4: 99 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 20 °C 5: iPr2NEt; HATU / dimethylformamide / 18 h / 20 °C View Scheme

1: 96 percent / KOH / dioxane; methanol / 2 h / 80 °C 2: SOCl2; DMAP / toluene / 1 h / Heating 3: 13.3 g / NH3(g) / CH2Cl2 / 20 °C 4: 94 percent / pyridine; TFAA / dioxane / 3 h / 20 °C 5: 99 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 20 °C 6: iPr2NEt; HATU / dimethylformamide / 18 h / 20 °C View Scheme