Tetrahydrofuran → 4-[(3-Isopropylphenyl)amino]-6-(2-morpholin-4-ylethoxy)-1,7-naphthyridine-3-carbonitrile

HRID 2113574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2113574
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[CH:16]=1.[OH:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C1COCC1>>[CH:21]([C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][N:11]=[C:2]([O:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][CH:18]=1)([CH3:23])[CH3:22]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 611632-MorpholinoethanolHCID 691808106-Fluoro-4-[(3-isopropylphenyl)amino]-1,7-naphthyridine-3-carbonitrile

Produkt 1

HCID 691856064-[(3-Isopropylphenyl)amino]-6-(2-morpholin-4-ylethoxy)-1,7-naphthyridine-3-carbonitrileAusbeute 66 %

Versuchsvorschrift

To 6-fluoro-4-[(3-isopropylphenyl)amino]-1,7-naphthyridine-3-carbonitrile (0.050 g, 0.16 mmol) was added a 1 M solution of freshly prepared alkoxide of N-(2-hydroxyethyl)morpholine in THF (1.88 mL, 1.88 mmol). The reaction was heated to reflux for 2 hours. The solvent was evaporated and water was added. Diethyl ehter and methylene chloride was added and crystals formed. The product was collected by filtration to give a yellow solid (0.044 g, 66%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.2 (d, J=6.8 Hz, 6 H) 2.5 (m, 2 H) 2.7 (t, J=5.8 Hz, 2 H) 2.9 (m, 1 H) 3.3 (m, 2 H) 3.6 (m, 4 H) 4.5 (t, J=5.8 Hz, 2 H) 7.1 (m, 3 H) 7.3 (t, J=8.7 Hz, 1 H) 7.8 (s, 1 H) 8.4 (s, 1 H) 9.0 (s, 1 H) 9.9 (s, 1 H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was evaporated
  4. additionwater was added
  5. additionDiethyl ehter and methylene chloride was added
  6. customcrystals formed
  7. filtrationThe product was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-34eb26f98844441dac8316eb07e6c267
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432279B2

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