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CAS No. : | 868171-67-9 | MDL No. : | MFCD19321394 |
Formula : | C12H8FNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 233.20 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; | E) tert-Butyl 4-((4-(2-fluoro4-(1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)phenoxy)-6-methoxyquinolin-7-yloxy)methyl)piperidine-1-carboxylate To a mixture of 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (15 mg, 0.06 mmol), HOBt (10 mg) and EDCI.HC1 (20 mg, 0.10 mmol) in DMF (2 mnL) was added a solution of <strong>[929252-65-3]tert-butyl 4-((4-(4-amino-2-fluorophenoxy)-6-methoxyquinolin-7-yloxy)methyl)piperidine-1-carboxylate</strong> (35 mg, 0.07 mmol) in DMF (1 mL) at rt, and the reaction mixture was stirred overnight at rt. It was directly purified by preparative HPLC to afford the product (24 mg, 56%) as a white TFA salt solid. 1H NMR (CDC13) delta12.16 (s, 1H), 8.75 (d, 1H, J=7.7 Hz), 8.64 (d, 1H, J=5.5 Hz), 8.05 (d, 1H, J=12.1 Hz), 7.83 (s, 1H), 7.67-7.24 (m, 8H), 6.72 (d, 1H, J=6.1 Hz), 6.65 (t, 1H, J=6.6 Hz), 4.22-4.11 (m, 2H), 4.07 (s, 3H), 3.48 (s, 2H), 2.78 (m, 2H), 2.13 (m, 1H), 1.87 (m, 2H), 1.47 (s, 9H), 1.35 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;dmap; In N,N-dimethyl-formamide; at 20℃; for 48h; | To a solution of 1 -(4-fluorophenyl)-2-oxo-1 ^-dihydropyridine-S-carboxylic acid (Intermediate E, 531 mg, 2.2 mmol) and 4-[(6,7-dimethoxyquinolin-4-yl)oxy]aniline (Intermediate A, 450 mg, 1.5 mmol) in DMF (20 ml_) were added 1 -(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (437 mg, 2.3 mmol), 1 - hydroxybenzotriazole (308 mg, 2.3 mmol), Et3N (231 mg, 2.27 mmol) and DMAP (18.5 mg, 0.15 mmol). The reaction mixture was stirred at rt for 48 h, and then ethyl acetate (50 ml_) was added. The mixture was washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was triturated with CH2CI2 and filtered to give 275 mg (35%) of the title compound. The filtrate was concentrated under reduced pressure and purified by silica gel flash chromatography to give an additional 180 mg (23 %) of the title compound. Total yield: 455 mg (58%).1H NMR (400 MHz, DMSO-cfe) delta 12.00 (s, 1 H), 8.50 (dd, 1 H), 8.46 (d, 1 H), 8.11 (dd, 1 H), 7.82 (d, 2 H), 7.62-7.59 (m, 2 H), 7.49 (s, 1 H), 7.43-7.39 (m, 2 H), 7.38 (s, 1 H), 7.25 (d, 2H), 6.71 (t, 1 H), 6.47 (d, 1 H), 3.93 (s, 3H), 3.91 (s, 3H); ES- MS m/z 512.0 [M+H]+, LCMS RT (min) 2.61. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; acetonitrile; at 20℃; for 3h; | General procedure: Appropriate aminoindolin-2-one (1equiv) was added to a mixture of appropriate 3-amino-3-oxopropanoic acid/2-pyridone acid/4-pyridone acid (1equiv), TBTU (1.5equiv) and TEA (3equiv) in DMF/acetonitrile (1:3, 0.16M). The resulting reaction mixture was stirred at room temperature for 3h. Reaction mixture was then concentrated in vacuo. Title compound was collected as solid by filtration and dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; acetonitrile; at 20℃; for 3.0h; | General procedure: Appropriate aminoindolin-2-one (1equiv) was added to a mixture of appropriate 3-amino-3-oxopropanoic acid/2-pyridone acid/4-pyridone acid (1equiv), TBTU (1.5equiv) and TEA (3equiv) in DMF/acetonitrile (1:3, 0.16M). The resulting reaction mixture was stirred at room temperature for 3h. Reaction mixture was then concentrated in vacuo. Title compound was collected as solid by filtration and dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 1.0h; | Step 5: 1-(4-Fluorophenyl)-N-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-oxo-1,2-dihydropyridine-3-carboxamide To a mixture of <strong>[819057-45-9]3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline</strong> (from Aldrich, 213.5 mg, 0.90 mmol) and 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (200 mg, 0.86 mmol) (prepared in Example 9, step 2) in N,N-dimethylformamide (4.7 mL) was added triethylamine (179 muL, 1.29 mmol) followed by N,N,N',N'-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (391 mg, 1.03 mmol). The resulting mixture, which became a mixture of solids quickly, was stirred at rt for 1 h. The solids were filtered and washed with water. Drying by vacuum suction gave the desired product as a white solid (305 mg, 79%). LCMS calcd for C24H24BF2N2O4 (M+H)+: m/z=453.2. Found: 453.2. |