Water → 6-Cyano-4-(1-ethylcarbamoylindol-5-yloxy)-7-[(piperidin-4-yl)methyloxy]quinoline

HRID 1433530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433530
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18](OC(OC(C)(C)C)=O)[CH2:17][CH2:16]1)[N:9]=[CH:8][CH:7]=[C:6]2[O:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35]([C:39](=[O:43])[NH:40][CH2:41][CH3:42])[CH:34]=[CH:33]2)#[N:2].[Na].O>FC(F)(F)C(O)=O>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[N:9]=[CH:8][CH:7]=[C:6]2[O:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35]([C:39](=[O:43])[NH:40][CH2:41][CH3:42])[CH:34]=[CH:33]2)#[N:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 5360545SodiumHCID 672029896-Cyano-4-(1-ethylcarbamoylindol-5-yloxy)-7-[(1-(t-butoxycarbonyloxy)piperidin-4-yl)methyloxy]quinoline

Produkt 1

HCID 672026266-Cyano-4-(1-ethylcarbamoylindol-5-yloxy)-7-[(piperidin-4-yl)methyloxy]quinolineAusbeute 373,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

After dissolving 6-cyano-4-(1-ethylcarbamoylindol-5-yloxy)-7-[(1-(t-butoxycarbonyloxy)piperidin-4-yl)methyloxy]quinoline (180 mg, 0.0753 mmol) in trifluoroacetic acid (1 ml), the solution was stirred at room temperature for 0.5 hour. Saturated sodium bicarnobate water was added, extraction was performed with ethyl acetate and tetrahydrofuran, the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, after which ethanol was added to the obtained amorphous substance for crystallization. After dilution with hexane, the crystals were filtered out, washed with hexane and dried by aspiration to obtain the title compound (132 mg, 0.2811 mmol, 88.96%) as colorless crystals.

Aufarbeitung

  1. extractionextraction
  2. washthe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionafter which ethanol was added to the obtained amorphous substance for crystallization
  6. filtrationAfter dilution with hexane, the crystals were filtered out
  7. washwashed with hexane
  8. customdried by aspiration

Quellen und Nachweise

ORD-Eintrag
ord-ec54577f15c040f9afb2836987f8ba4e
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612092B2

Notizen zur Reaktion

Wird geladen…