1,2-Dichloroethane → N-(6-Chloro-1H-indazol-5-yl)-4-(4-chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

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Reaction Steps

6-Chloro-1H-indazol-5-amine (64 mg, 0.382 mmol, 1.0 equiv) was combined with the product from Example 4, Step 2 (101 mg, 0.382 mmol, 1.0 equiv), EDC (88 mg, 0.458 mmol, 1.2 equiv) and Et3N (64 μL, 0.458 mmol, 1.2 equiv) in DMF (1 mL) and stirred at room temperature for 18 hours. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. The organic phase was concentrated en vacuo. The residue was purified by flash chromatography (0-100% EtOAc in Hexanes) and further purified by reverse-phase HPLC (15-98% CH3CN/H2O, adjusted to pH 10 w/NH4OH over 13 minutes, retention time 6.56 min) to provide 40 mg (25%) of the title compound as a white solid. MS (ES+) m/e 416 [M+H]+

Provenance & Evidence