ChemicalBook CAS DataBase List N-[4-[(2-Amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

N-[4-[(2-Amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide synthesis

12synthesis methods

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]?-

1025721-14-5
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N-[4-[(2-Amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

1025720-94-8
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$28.00/1unit

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

55934-00-4 Synthesis