Hydrochloric Acid → 6-Cyano-4-(1H-indol-5-yloxy)-7-(piperidin-4-yl)methyloxyquinoline

HRID 1010260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010260
[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)[NH:35][CH:34]=[CH:33]2)#[N:2].Cl>C(O)C.O1CCCC1>[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)[NH:35][CH:34]=[CH:33]2)#[N:2]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 672017656-Cyano-4-(1H-indol-5-yloxy)-7-[(1-(t-butoxycarbonyloxy)piperidin-4-yl)methyloxy]quinoline

Produkt 1

HCID 229366766-Cyano-4-(1H-indol-5-yloxy)-7-(piperidin-4-yl)methyloxyquinolineAusbeute 7,51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Cyano-4-(1H-indol-5-yloxy)-7-[(1-(t-butoxycarbonyloxy)piperidin-4-yl)methyloxy]quinoline (0.25 g, 0.5015 mmol) was dissolved in ethanol (2 ml) and tetrahydrofuran (2 ml), and then concentrated hydrochloric acid (0.2 ml) was added at room temperature and the mixture was stirred for 17 hours. The solvent was distilled off under reduced pressure, saturated sodium bicarnobate water was added, and then extraction was performed with a tetrahydrofuran and ethyl acetate mixed solvent, the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was adsorbed onto NH silica gel and purified by column chromatography (ethyl acetate-methanol system) with NH silica gel, and the obtained crystals were suspended in ethanol and diluted with diethyl ether and hexane. The crystals were filtered out, washed with diethyl ether and dried by aspiration to obtain the title compound (15 mg, 0.0376 mmol, 7.51%).

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure, saturated sodium bicarnobate water
  2. additionwas added
  3. extractionextraction
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. custompurified by column chromatography (ethyl acetate-methanol system) with NH silica gel
  8. additiondiluted with diethyl ether and hexane
  9. filtrationThe crystals were filtered out
  10. washwashed with diethyl ether
  11. customdried by aspiration

Quellen und Nachweise

ORD-Eintrag
ord-7f485fae67c7402387dd6b8267970c3f
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973160B2

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