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Pyridine → 4-(4-Ethynyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid pentafluorophenyl ester

HRID 917786
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 917786
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11]([C:18]([OH:20])=[O:19])=[CH:12][N:13]([CH3:17])[C:14](=[O:16])[CH:15]=2)=[C:5]([F:21])[CH:4]=1)#[CH:2].FC(F)(F)C(O[C:27]1[C:32]([F:33])=[C:31]([F:34])[C:30]([F:35])=[C:29]([F:36])[C:28]=1[F:37])=O.N1C=CC=CC=1>CN(C=O)C>[F:33][C:32]1[C:27]([O:19][C:18]([C:11]2[C:10]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([C:1]#[CH:2])=[CH:4][C:5]=3[F:21])=[CH:15][C:14](=[O:16])[N:13]([CH3:17])[CH:12]=2)=[O:20])=[C:28]([F:37])[C:29]([F:36])=[C:30]([F:35])[C:31]=1[F:34]
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Komponenten

5

Edukt 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 114603454-(4-Ethynyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Produkt 1

HCID 865963824-(4-Ethynyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid pentafluorophenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

4-(4-Ethynyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (0.70 g, 2.44 mmol) was reacted with pentafluorophenyl trifluoroacetate (1.30 mL, 7.36 mmol) in the presence of pyridine (0.60 mL) in DMF. The solution was allowed to stir at room temperature for 15 hours, to afford the 4-(4-Ethynyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid pentafluorophenyl ester which was reacted directly with 2-aminoethanol (0.74 mL, 12.20 mmol) that is stirred at room temperature for 4 hours. The resulting precipitate was filtered and purified by column chromatography on silica gel (5% MeOH/CH2Cl2 as eluant) to give 4-(4-Ethynyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (2-hydroxy-ethyl)-amide as a yellow solid (0.24 g, 30%). 1H NMR [(CD3)2SO, 400 MHz] δ 10.27 (s, 1H), 8.41 (t, 1H), 8.13 (s, 1 H), 7.48 (dd, J=10.2, 1.8 Hz, 1H), 7.40 (dd, J=8.6 Hz, 1H), 7.31 (dd, J=8.5 Hz, 1H), 5.73 (s, 1H), 4.76 (t, 1 H, OH), 4.24 (s, 1H), 3.51 (t, J=4.9 Hz, 2H), 3.35 (s, 3H), 3.25 (t, J=8.3 Hz, 2H). (APCI+) calcd for C17H16FN3O3 329.33 (M+1), found 330.1.

Quellen und Nachweise

ORD-Eintrag
ord-d5e6a7c9526b440cab697b0c6cf2a7a1
Quelldatensatz
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07273877B2

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