N-(3-Aminopropyl)morpholine → 1-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[3-(4-morpholinyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide [3-(4-morpholinyl)propyl]amine

HRID 2364383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2364383
[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].[N:39]1([CH2:45][CH2:46][CH2:47][NH2:48])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>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:48][CH2:47][CH2:46][CH2:45][N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[O:34])[C:15]1=[O:38].[N:39]1([CH2:45][CH2:46][CH2:47][NH2:48])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1

Komponenten

4

Edukt 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 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 694827121-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[3-(4-morpholinyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide [3-(4-morpholinyl)propyl]amine

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 (0.025 g, 0.049 mmol) in EtOH (2.5 mL) under nitrogen was treated with [3-(4-morpholinyl)propyl]amine (0.035 mL, 0.24 mmol) for 40 min.@130° C. in a microwave vessel. The reaction was then cooled to ambient temperature and the resulting suspension was filtered, washed with EtOH and Et2O then thoroughly dried under high vacuum to provide the title compound as a white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 1.5 (m, 4 H), 2.2 (t, J=7.0 Hz, 2 H), 2.3 (m, 1 H), 2.6 (t, J=6.9 Hz, 2 H), 3.2 (q, J=6.5 Hz, 2 H), 3.5 (q, J=4.9 Hz, 8 H), 3.9 (t, J=5.5 Hz, 2 H), 4.1 (s, 2 H), 4.5 (t, J=5.6 Hz, 2 H), 7.1 (ddd, J=9.1, 6.7, 2.1 Hz, 2 H), 7.3 (m, 2 H), 7.8 (m, 4 H), 8.1 (s, 1 H), 8.4 (t, J=1.1 Hz, 1 H), 10.0 (t, J=6.0 Hz, 1 H); ES+ MS: 614 (M+H+).

Aufarbeitung

  1. filtrationthe resulting suspension was filtered
  2. washwashed with EtOH and Et2O
  3. customthen thoroughly dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1a178bbda07146ffa7d09d23b9d3926d
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691991B2

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