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N,N'-Dimethylethylenediamine → HCID 71736211, Verbindung

HRID 525331
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 525331
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:12]([CH3:14])([CH3:13])[O:11][C:10](=[O:15])[NH:9]2)=[CH:4][CH:3]=1.I[C:17]1[CH:35]=[CH:34][C:20]([C:21]([NH:23][C:24]2[CH:25]=[CH:26][CH:27]=[C:28]3[C:33]=2[N:32]=[CH:31][CH:30]=[CH:29]3)=[O:22])=[CH:19][CH:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[C:12]([CH3:13])([CH3:14])[O:11][C:10](=[O:15])[N:9]2[C:17]2[CH:35]=[CH:34][C:20]([C:21]([NH:23][C:24]3[CH:25]=[CH:26][CH:27]=[C:28]4[C:33]=3[N:32]=[CH:31][CH:30]=[CH:29]4)=[O:22])=[CH:19][CH:18]=2)=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 41661718HCID 41661718, VerbindungHCID 89814018HCID 89814018, Verbindung

Produkt 1

HCID 71736211HCID 71736211, VerbindungAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A microwave vial was charged with (S)-4-(4-fluorophenyl)-5,5-dimethyloxazolidin-2-one (0.050 g, 0.239 mmol), 4-iodo-N-(quinolin-8-yl)benzamide (0.098 g, 0.263 mmol), tribasic potassium phosphate (0.254 g, 1.195 mmol) and dioxane (2.50 mL). The mixture was purged with argon and then copper (I) iodide (0.046 g, 0.239 mmol) and N,N′-dimethylethylenediamine (0.051 mL, 0.478 mmol) were added. The system was purged with argon, the tube was sealed, and the reaction mixture was heated at 140° C. for 2 hours in the microwave. The reaction mixture was filtered through Celite® brand filter aid, and the filtrate was concentrated to afford an orange brown solid. The residual material was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% EtOAc-hexane) to afford (S)-4-(4-(4-fluorophenyl)-5,5-dimethyl-2-oxooxazolidin-3-yl)-N-(quinolin-8-yl)benzamide (0.097 g, 0.213 mmol, 89% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.95 (s, 3H) 1.66 (s, 3H) 5.60 (s, 1H) 7.16-7.29 (m, 2H) 7.36 (br. s., 2H) 7.58-7.81 (m, 5H) 7.97 (d, J=8.80 Hz, 2H) 8.45 (dd, J=8.31, 1.66 Hz, 1H) 8.67 (dd, J=7.68, 1.32 Hz, 1H) 8.95 (dd, J=4.21, 1.66 Hz, 1H) 10.55 (s, 1H). m/z (ESI) 456 (M+H)+.

Aufarbeitung

  1. customThe mixture was purged with argon
  2. customThe system was purged with argon
  3. customthe tube was sealed
  4. filtrationThe reaction mixture was filtered through Celite® brand
  5. filtrationfilter aid
  6. concentrationthe filtrate was concentrated
  7. customto afford an orange brown solid
  8. customThe residual material was purified

Quellen und Nachweise

ORD-Eintrag
ord-845f23ee1a26449e8410ec343fabf89e
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09340549B2

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