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With palladium on activated charcoal; hydrazine hydrate In ethanol at 50℃; for 1.5 h; Inert atmosphere
Example 307b 1,3-Dimethyl-1H-indazol-5-amine 307b To a solution of 307a (crude, 2.5 mmol) in ethanol (95percent, 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, 84percent over two steps). MS-ESI: [M+H]+ 162.3
With palladium on activated charcoal; hydrazine hydrate; In ethanol; at 50.0℃; for 1.5h;Inert atmosphere;
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
(4-{6-[(1,3-dimethyl-1H-indazol-5-yl)amino]-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl}-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl)methyl acetate[ No CAS ]
5-bromo-3-(1,3-dimethyl-1H-indazol-5-yl)amino-1-methylpyrazin-2(1H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
92%
With triethylamine; In isopropyl alcohol; for 6h;Reflux;
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.
N-(1,3-dimethyl-1H-indazol-5-yl)methanesulfonamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
59.3%
With triethylamine; In dichloromethane; at 20.0℃; for 3.0h;
A solution of <strong>[5757-85-7]1,3-dimethyl-1H-indazol-5-amine</strong> (0.250 g, 1.551 mmol), methanesulfonyl chloride (0.132 mL, 1.706 mmol) and triethylamine (0.324 mL, 2.326 mmol) in dichloromethane (3 mL) was stuffed at the room temperature for 3 hr. Then, water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 4 g cartridge; ethyl acetate / hexane = 0 % to 50 %) to give N- (1 ,3-dimethyl- 1 H-indazol-5-yl)methanesulfonamide as white solid (0.220 g, 59.3 %).
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