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Sodium Iodide → Unc9975

HRID 1750077
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1750077
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][C:18]2[CH2:17][CH2:16][C:15](=[O:21])[NH:14][C:13]=2[N:12]=1)(=O)=O.[Na+].[I-].CCN(CC)CC.[Cl:31][C:32]1[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=1[N:39]1[CH2:45][CH2:44][CH2:43][N:42](CCCCOC2C=C3C(CCC(=O)N3)=CC=2)[CH2:41][CH2:40]1>CC#N>[Cl:31][C:32]1[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=1[N:39]1[CH2:45][CH2:44][CH2:43][N:42]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[N:12]=[C:13]3[C:18]([CH2:17][CH2:16][C:15](=[O:21])[NH:14]3)=[CH:19][CH:20]=2)[CH2:41][CH2:40]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 56597938Unc0006HCID 870843174-(7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yloxy)butyl methanesulfonate

Produkt 1

HCID 56593482Unc9975Ausbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Intermediate 12 (85 mg, 0.27 mmol) was dissolved in CH3CN then NaI (55 mg, 0.37 mmol), Et3N (91 mg, 0.9 mmol), and intermediate 2 (102 mg, 0.36 mmol) were added. The resulting mixture was stirred at 70° C. overnight. Precipitated crystals were filtered off and the filtrate was evaporated under reduced pressure. The residue was 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=30:1) to give 7-(4-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)butoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one (compound 3) (78 mg, 63%). 1H NMR (300 MHz, CDCl3): δ 7.64 (s, 1H), 7.38 (d, J=8.1 Hz, 1H), 7.27-7.15 (m, 2H), 7.06 (d, J=8.1 Hz, 1H), 6.37 (d, J=8.1 Hz, 1H), 4.36 (t, J=6.0 Hz, 2H), 3.61-3.49 (m, 7H), 3.32-3.20 (m, 5H), 2.90-2.85 (m, 2H), 2.67-2.62 (m, 2H), 2.21-2.16 (m, 2H), 1.90-1.85 (m, 2H). HPLC: 99%, RT 2.682 min. MS (ESI) m/z 463.1 [M+H]+. mp: 110-111° C.

Aufarbeitung

  1. customPrecipitated crystals
  2. filtrationwere filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. extractionThe residue was extracted with EtOAc
  5. washThe combined EtOAc layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-51f47852e0354fdf84ce6ec88ca8f927
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156822B2

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