N-[4-[(2-Amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide synthesis
- Product Name:N-[4-[(2-Amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
- CAS Number:1025720-94-8
- Molecular formula:C25H19ClF2N4O4
- Molecular Weight:512.89
![2-?Pyridinecarboxamide, 3-?chloro-?4-?[4-?[[[4-?ethoxy-?1-?(4-?fluorophenyl)?-?1,?2-?dihydro-?2-?oxo-?3-?pyridinyl]?carbonyl]?amino]?-?2-?fluorophenoxy]?-](/CAS/20200611/GIF/1025721-14-5.gif)
1025721-14-5
1025720-94-8
3-Chloro-4-(4-(4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-2-fluorophenoxy)pyridin-2-amine (1.2 g, 2.1 mmol) was used as a starting material and was dissolved in a solvent mixture of ethyl acetate (16 mL), acetonitrile (16 mL) and water (8 mL) at 0 °C. Subsequently, iodophenyl diacetate (820 mg, 2.6 mmol, Aldrich) was added. The reaction mixture was stirred at room temperature for 2 h before the crude product was collected by filtration. The solid was washed with additional ethyl acetate. The filtrate was washed with saturated aqueous sodium bicarbonate and the organic phase was dried with anhydrous sodium sulfate and subsequently concentrated under vacuum. The precipitate was combined with the concentrated filtrate and purified by rapid chromatography on silica gel (eluent: 2% methanol/chloroform) to afford the target compound, N-(4-((2-amino-3-chloropyridin-4-yl)oxy)-3-fluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (810 mg, yield 74%). It was a white solid. The product was characterized by 1H NMR (DMSO-d6) and MS (ESI+): 1H NMR (DMSO-d6) δ 10.57 (s, 1H), 7.83-7.79 (m, 2H), 7.67 (d, 1H, J = 5.6Hz), 7.41-7.38 (m, 3H), 7.36-7.22 (m, 3H), 6.44 (d, 1H, J = 5.6Hz). 1H, J = 7.6 Hz), 6.36 (br s, 2H), 5.86 (d, 1H, J = 6.0 Hz), 4.18 (q, 2H, J = 7.2 Hz), 1.23 (t, 3H, J = 7.2 Hz); MS (ESI +) m/z 513.09 (M + H)+.
1025721-14-5
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1025720-94-8
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Yield:1025720-94-8 74%
Reaction Conditions:
with [bis(acetoxy)iodo]benzene in water;ethyl acetate;acetonitrile at 0 - 20; for 2 h;
Steps:
1.J
To 3-chloro-4-(4-(4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-2-fluorophenoxy)picolinamide (1.2 g, 2.1 mmol) in ethyl acetate (16 mL), acetonitrile (16 mL), and water (8 mL) at 0° C. was added iodobenzene diacetate (820 mg, 2.6 mmol, Aldrich). After stirring at rt for 2 h, the reaction was filtered to collect the crude product. The solid was washed with additional ethyl acetate. The filtrate was washed with saturated aqueous sodium bicarbonate solution and the organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The precipitate and filtrate were combined and purified by flash chromatography on silica gel (2% methanol/chloroform) to give the title compound (810 mg, 74%) as a white solid. 1H NMR (DMSO-d6) δ 10.57 (s, 1H), 7.83-7.79 (m, 2H), 7.67 (d, 1H, J=5.6 Hz), 7.41-7.38 (m, 3H), 7.36-7.22 (m, 3H), 6.44 (d, 1H, J=7.6 Hz), 6.36 (br s, 2H), 5.86 (d, 1H, J=6.0 Hz), 4.18 (q, 2H, J=7.2 Hz), 1.23 (t, 3H, J=7.2 Hz); MS (ESI+) m/z 513.09 (M+H)+.
References:
US2008/114033,2008,A1 Location in patent:Page/Page column 9
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1025720-94-8
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