Cyclohexylamine → HCID 59699642, Verbindung

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Reaktionsgleichung

[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:33])[N:15]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[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:33])[N:15]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[C:16]3[C:21]([C:22]=2[OH:23])=[CH:20][CH:19]=[CH:18][N:17]=3)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

Cyclohexylamine (1.18 mL, 10.35 mmol) was added to a stirred solution of 4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (13) (1.80 g, 5.17 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 washed by water and brine, then dried over Na2SO4 and evaporated to yield 1.68 g (82%) of 4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid cyclohexylamide (29) as white solids. MP: 149° C.; 1H-NMR (DMSO-d6): δ 1.2-1.4 (m, 5H), 1.55 (m, 1H), 1.70 (m, 2H), 1.90 (m, 2H), 3.69 (s, 3H), 3.86 (m, 1H), 5.54 (s, 2H), 6.81 (d, J=8.8 Hz, 2H), 7.20 (d, J=8.8 Hz, 2H), 7.43 (m, 1H), 8.47 (dd, J=2.0, 8.0 Hz, 1H), 8.79 (dd, J=1.6, 4.8 Hz, 1H), 10.22 (d, J=7.2 Hz, 1H); EIMS m/z 408 (M+1).

Aufarbeitung

temperatureThe solution was cooled
customthe solvent was evaporated under vacuum
extractionextracted by dichloromethane
washThe combined organic phase washed by water and brine
dry with materialdried over Na2SO4
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-4842fd0cb2ee4e5bbe80c81fbc809c9c
Quelldatensatz: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07361760B2

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