Cyclohexylamine → 6-Fluoro-4-hydroxy-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Cyclohexylamide

HRID 901270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 901270
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:10][C:11]([C:13]1[C:14](=[O:34])[N:15]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][C:19]([F:24])=[CH:18][N:17]=2)=O)C>C1(C)C(C)=CC=CC=1>[CH:1]1([NH:7][C:11]([C:13]2[C:14](=[O:34])[N:15]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:16]3[C:21]([C:22]=2[OH:23])=[CH:20][C:19]([F:24])=[CH:18][N:17]=3)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 7965CyclohexylamineHCID 692163256-Fluoro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester

Produkt 1

HCID 692178066-Fluoro-4-hydroxy-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid CyclohexylamideAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Cyclohexylamine (6.14 mL, 53.65 mmol) was added to a stirred solution of 6-fluoro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (74) (10 g, 26.82 mmol) in xylene and heated at 140° C. for 3 h. The solution was cooled and the solvent was evaporated under vacuum. The residue was suspended in water and extracted by dichloromethane. The combined organic phase was washed by water and brine, then dried over Na2SO4 and evaporated to yield 7.46 g (65%) of 6-fluoro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid cyclohexyl amide (92) as white solids. MP: 176° C.; 1H-NMR (DMSO-d6): δ 1.25-1.41 (m, 5H), 1.54 (m, 1H), 1.66 (m, 2H), 1.87 (m, 2H), 3.68 (s, 3H), 3.86 (m, 1H), 5.51 (s, 2H), 6.81 (d, J=8.8 Hz, 2H), 7.20 (d, J=8.8 Hz, 2H), 8.31 (d, J=8.0 Hz, 1H), 8.83 (s, 1H), 10.24 (s, 1H); EIMS m/z 426 (M+1).

Aufarbeitung

  1. temperatureThe solution was cooled
  2. customthe solvent was evaporated under vacuum
  3. extractionextracted by dichloromethane
  4. washThe combined organic phase was washed by water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1f6b3ab77f834fe48ce8155340484452
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361760B2

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