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Sodium Iodide → 7-(4-(4-(2-ethoxyphenyl)-1,4-diazepan-1-yl)butoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 1750100
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1750100
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2C=[C:30]3[C:25]([CH2:26][CH2:27][C:28](=[O:32])[NH:29]3)=[CH:24][CH:23]=2)[CH2:12][CH2:11]1)[CH3:2].[Na+].[I-].Cl.C(OC1C=CC=CC=1[N:45]1CCCNCC1)C.C([O-])([O-])=O.[K+].[K+]>CC#N.O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[N:45]=[C:30]3[C:25]([CH2:26][CH2:27][C:28](=[O:32])[NH:29]3)=[CH:24][CH:23]=2)[CH2:12][CH2:11]1)[CH3:2]
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Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 565988787-(4-(4-(2-ethoxyphenyl)-1,4-diazepan-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-oneHCID 666337571-(2-Ethoxyphenyl)-1,4-diazepane hydrochloride

Produkt 1

HCID 565980737-(4-(4-(2-ethoxyphenyl)-1,4-diazepan-1-yl)butoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one
Ausbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of intermediate 12 (150 mg, 0.48 mmol) and NaI (150 mg, 1.0 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 31 (124 mg, 0.48 mmol) and anhydrous K2CO3 (265 mg, 1.92 mmol) were added to the mixture. The resulting mixture was heated to reflux and stirred overnight. The reaction solution was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH=50:1) to give 7-(4-(4-(2-ethoxyphenyl)-1,4-diazepan-1-yl)butoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one (compound 13) (50 mg, 24%). 1H NMR (300 MHz, CDCl3) δ 7.55 (bs, 1H), 7.35 (d, J=8.1 Hz, 1H), 6.89-6.85 (m, 4H), 6.34 (d, J=8.1 Hz, 1H), 4.24-4.20 (m, 2H), 4.04 (q, J=6.9 Hz, 2H), 3.41-3.37 (m, 2H), 3.31 (t, J=5.7 Hz, 2H), 3.15-2.95 (m, 4H), 2.86 (t, J=6.9 Hz, 2H), 2.79-2.69 (m, 2H), 2.64 (t, J=7.5 Hz, 2H), 2.20-2.12 (s, 2H), 1.82-1.76 (m, 4H), 1.45 (t, J=6.9 Hz, 3H). HPLC: 99%, RT 2.393 min. MS (ESI) m/z 439.2 [M+H]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc layers were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo
  9. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-462d65073bc740c6810c2e69e034869a
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156822B2

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