5-AMino-1,3-diMethylindaz...

A solution of Example 307c 5-Bromo-3-(1, 3-dimethyl-1H-indazol-5-ylamino-1-methylpyrazin-2(1H)-one 307c To a solution of 307b (280 mg, 1.74 mmol) in i-propanol (7 mL) was added triethylamine (352 mg, 3.48 mmol) and 3, 5-dibromo-1-methylpyrazin-2(1H)-one (H-005) (700 mg, 2.61 mmol). After being stirred at reflux for 6 h, the mixture was cooled to room temperature. The precipitate was filtered, washed with i-propanol (2 X 2 mL), and dried at 60°C under reduced pressure to afford 307c as a brown solid (560 mg, 92percent). MS-ESI: [M+H]+ 347.8.Example 307b 1, 3-Dimethyl-1H-indazol-5-amine 307b To a solution of 307a (crude, 2.5 mmol) in ethanol (95%, 30 mL) was added NH2NH2 water (1.25 g, 25.0 mmol), Pd/C (100 mg) under nitrogen protection. The mixture was stirred at 50 C for 1.5 h. It was then cooled to room temperature and filtered through a pad of CELITE. The filtrate was concentrated under reduced pressure and the residue was recrystallized from anhydrous ethanol (5 mL) to afford 307b as white solid (340 mg, 84% over two steps). MS-ESI: [M+H]+ 162.3