Ethoxyethylamine → 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2364336
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33](OCC)=[O:34])[C:15]1=[O:38].[CH2:39]([O:41][CH2:42][CH2:43][NH2:44])[CH3:40]>CCO>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33]([NH:44][CH2:43][CH2:42][O:41][CH2:39][CH3:40])=[O:34])[C:15]1=[O:38]

Komponenten

4

Edukt 2

HCID 66970EthoxyethylamineHCID 69480967ethyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Produkt 1

HCID 694828111-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (0.021 g, 0.041 mmol) in EtOH (2 mL) under nitrogen was treated with Ethoxyethylamine (0.021 mL, 0.2 mmol) for 10 min.@150° C. in a microwave vessel then@180° C. for an additional 10 min. After the reaction was cooled to ambient temperature the resulting suspension was filtered, and the filtered solid was washed with water and Et2O then thoroughly dried under high vacuum to provide the title compound as a beige solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.07 (t, J=6.95 Hz, 4 H), 1.56-1.91 (m, 1 H), 3.34-3.41 (m, 7 H), 3.88-3.92 (m, 2 H), 4.11 (s, 2 H), 4.53-4.56 (m, 1 H), 7.12-7.13 (m, 1 H), 7.32-7.37 (m, 2 H), 7.81-7.82 (m, 4 H), 8.14-8.15 (m, 1 H), 8.52 (dd, J=1.47, 0.35 Hz, 1 H), 9.76-10.16 (m, 1 H); ES+ MS: 559 (M+H+).

Aufarbeitung

  1. filtrationwas filtered
  2. washthe filtered solid was washed with water and Et2O
  3. customthen thoroughly dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0f02aa6b84f84abeb5def9fc18a87bb9
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691991B2

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