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Triethylamine → HCID 86707196, Verbindung

HRID 715885
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 715885
[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]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30]([CH2:33][NH:34][CH3:35])=[CH:29][N:28]=4)[CH2:23][CH2:22]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.C(N(CC)CC)C.[CH3:56][S:57](Cl)(=[O:59])=[O:58].C(=O)([O-])O.[Na+]>ClCCl>[F:48][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:22][CH2:23][N:24]([C:27]4[N:32]=[CH:31][C:30]([CH2:33][N:34]([CH3:35])[S:57]([CH3:56])(=[O:59])=[O:58])=[CH:29][N:28]=4)[CH2:25][CH2:26]3)[C:9]=2[CH:36]([F:47])[C:37]2[CH:38]=[CH:39][C:40]([C:43]([F:45])([F:44])[F:46])=[CH:41][CH:42]=2)[CH2:6][CH2:7]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86682466HCID 86682466, Verbindung

Produkt 1

HCID 86707196HCID 86707196, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of 65 mg (95 μmol) of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-(1-{5-[(methylamino)methyl]pyrimidin-2-yl}piperidin-4-yl)-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Example 58, in 0.2 ml of dichloromethane, 30 μl (0.19 mmol) of triethylamine and 8 μl (0.1 mmol) of methanesulfonyl chloride were added, and the reaction solution was stirred at room temperature for 1 hour. After completion of the reaction, saturated sodium hydrogencarbonate aqueous solution was poured into the reaction solution and the reaction solution 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=100/0-40/60 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 37 mg of the title compound as a white solid (yield: 52%).

Aufarbeitung

  1. additionwas poured into the reaction solution
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0c2d9eaad9fe4914adef527aa78fa910
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09187450B2

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