4-Methylmorpholine → 6-bromo-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-1H-indazole-4-carboxamide

Beteiligte Stoffe

Reaktionsschritte

6-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid (1.44 g, 4.61 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone hydrochloride (1.138 g, 6.03 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (1.335 g, 6.96 mmol), and 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol hydrate (1.073 g, 6.96 mmol) were suspended in DMSO (8.00 mL), followed by N-methylmorpholine (2.82 g, 27.8 mmol). The reaction mixture was stirred at room temperature overnight to afford a slurry. The slurry was diluted with DMSO (10 mL) and added dropwise to a ice-chilled aqueous solution of 1N Na2CO3 (50 ml) and water (200 mL), and stirred rapidly for 30 min. The precipitate was collected by vacuum filtration and washed with water. The cake was dried in the vacuum oven at 60° C. overnight (16 h). The title compound was obtained as a pale yellow-white solid (2.05 g, 98% yield). 1H NMR (400 MHz, DMSO-δ6) δ 11.50 (br. s., 1H), 8.64 (br. s., 1H), 8.37 (s, 1H), 8.20 (s, 1H), 7.70 (d, J=1.52 Hz, 1H), 5.89 (s, 1H), 5.22 (quin, J=7.01 Hz, 1H), 4.34 (d, J=4.55 Hz, 2H), 2.20 (s, 3H), 2.13 (s, 3H), 2.06-2.11 (m, 2H), 1.91-2.03 (m, 2H), 1.80-1.91 (m, 2H), 1.61-1.75 (m, 2H). LC-MS(ES) [M+H]+ 443.0.

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