Quinolin-2-one derivatives
A technology of compounds and mixtures, applied in the field of compounds that can be used to treat diseases such as cancer, treat diseases, and prepare these compounds, which can solve high and unmet medical needs
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Embodiment 1
[0621] 6-fluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one ("A1")
[0622]
[0623] To 3-ethynyl-6-fluoro-1H-quinolin-2-one (46.8 mg, 0.25 mmol), copper(II) sulfate pentahydrate (4.0 mg, 0.03 mmol) and (2R)-2-[( 2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxy-ethanolate sodium hydrate (5.4 mg, 0.03 mmol) in suspension in DMF (0.5 ml) (4-Azido-phenyl)-morpholin-4-yl-methanone (65.0 mg, 0.28 mmol) was added. The reaction mixture was heated to 110 °C and stirred at this temperature for 22 hours. The reaction mixture was allowed to reach room temperature. Water was added and the resulting precipitate was filtered off, washed with water and dried. The residue was chromatographed on a silica gel column with dichloromethane / methanol as eluent to afford 6-fluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl) as an off-white powder ]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one; HPLC / MS 1.44 min (A),[M+H] + 420.
[0624] 1 H NMR (400 MHz, DMSO-...
Embodiment 2
[0744] 3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,6]naphthyridine-2- Ketones ("A41")
[0745]
[0746] To 4-amino-pyridine-3-carbaldehyde (61.1 mg, 0.50 mmol), {1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazole-4 -yl}-acetic acid (158 mg, 0.50 mmol) and [dimethylamino-([1,2,3]triazolo[4,5-b]pyridin-3-yloxy)-methylene] -Dimethyl-ammonium hexafluorophosphate (HATU; 380 mg, 1.0 mmol) in DMF (1.3 ml) was added N-ethyldiisopropylamine (257 µl, 1.5 mmol), and the reaction mixture was incubated at room temperature Stirring was continued for 17 hours. Water was added to the reaction mixture. The resulting precipitate was filtered off, dried and chromatographed on a silica gel column with dichloromethane / methanol as eluent to afford 3-{1-[4-(morpholine-4-carbonyl)- Phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,6]naphthyridin-2-one; HPLC / MS 1.02 min (A), [M+H]+ 403.
[0747] 1 H NMR (400 MHz, DMSO-d 6 ) δ 12.46 (s, 1H), 9.28 (s, 1H), 9.10 (s, 1H), 8.9...
Embodiment 3
[0774] 3-{1-[4-(Piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (“A50” )
[0775]
[0776] 4-{4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}- A suspension of tert-butyl piperazine-1-carboxylate (43 mg, 0.09 mmol; synthesized similarly to Example 1) in a 4M solution (0.5 ml) of hydrochloric acid in dioxane was heated to 80°C and heated in Stir at this temperature for 1 hour in a closed reaction vial. The reaction mixture was allowed to reach room temperature. The solid was filtered off and washed with THF. The residue was treated with aqueous sodium carbonate. The solid was filtered off, washed with water and ethanol and dried under vacuum to give 3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2, 3] Triazol-4-yl}-1H-quinolin-2-one; HPLC / MS 1.07 min (B), [M+H] + 401.
[0777] 1 H NMR (400 MHz, DMSO-d 6 ) δ 12.21 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.08 (d, J = 8.0 Hz, 2H), 7.90 (d, J = 7.9 Hz, 1H), 7.61 (d , J = 8.0 Hz...
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