Hydrochloric Acid → HCID 76372215, Verbindung

HRID 715846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 715846
[F:1][C:2]1([F:48])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([O:18]CC4C=CC(OC)=CC=4)[CH2:15][C:14]([CH3:29])([CH3:28])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:9]=2[CH:36]([F:47])[C:37]2[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=2)[CH2:4][CH2:3]1.Cl[C:50]1[N:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][N:51]=1.Cl.C(=O)([O-])O.[Na+]>O1CCOCC1>[F:1][C:2]1([F:48])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:29])([CH3:28])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][N:33]([C:50]4[N:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][N:51]=4)[CH2:32][CH2:31]3)[C:9]=2[CH:36]([F:47])[C:37]2[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=2)[CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5890582-Chloro-5-methoxypyrimidineHCID 86682426(-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(piperidin-4-yl)-5,6,7,8-tetrahydroquinoline

Produkt 1

HCID 76372215HCID 76372215, VerbindungAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 100 mg (0.15 mmol) of (−)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(piperidin-4-yl)-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 10, 64 mg (0.44 mmol) of 2-chloro-5-methoxypyrimidine and 1 ml of 1,4-dioxane were added, and the reaction solution was stirred at 80° C. for 26.6 hours. After completion of the reaction, 0.5 ml of 6 N hydrochloric acid was added to the reaction solution and the mixture was stirred at 50° C. for 8 hours. After completion of the reaction, saturated sodium hydrogencarbonate aqueous solution was added to the reaction mixture and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=4/1 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure. n-Hexane was added to the obtained residue and the precipitate was obtained by filtration to provide 44 mg of the title compound as a white powder (yield: 45%).

Aufarbeitung

  1. additionwere added
  2. additionwas added to the reaction solution
  3. stirringthe mixture was stirred at 50° C. for 8 hours
  4. additionwas added to the reaction mixture
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated sodium chloride aqueous solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. concentrationwas concentrated under reduced pressure
  10. additionn-Hexane was added to the obtained residue
  11. customthe precipitate was obtained by filtration

Quellen und Nachweise

ORD-Eintrag
ord-74189dc7b5554e75a1607f7220ecb473
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187450B2

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