Hydrochloric Acid → HCID 178448469, Verbindung

HRID 84230

Reaktionsgleichung

Reaktionsgleichung von HRID 84230
Cl.[CH3:2][C@@:3]([S:44]([CH3:47])(=[O:46])=[O:45])([CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C@H:30]3[CH2:35][CH2:34][C@@H:33]([O:36]C4CCCCO4)[CH2:32][CH2:31]3)=[CH:24][CH:23]=2)=[CH:18][C:17]1=[O:43])[C:4]([NH:6][O:7]C1CCCCO1)=[O:5]>O1CCOCC1>[OH:7][NH:6][C:4](=[O:5])[C@:3]([CH3:2])([S:44]([CH3:47])(=[O:46])=[O:45])[CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C@H:30]3[CH2:31][CH2:32][C@@H:33]([OH:36])[CH2:34][CH2:35]3)=[CH:24][CH:23]=2)=[CH:18][C:17]1=[O:43]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 178448466HCID 178448466, Verbindung

Produkt 1

HCID 178448469HCID 178448469, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

HCl (1.0 N in water, 1.02 mL) was added to a solution of (2R)-2-methyl-2-(methylsulfonyl)-4-[2-oxo-4-(4-{[cis-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]methoxy}phenyl)pyridin-1(2H)-yl]-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (135 mg, 0.204 mmol) in 1,4-dioxane (5.0 mL). After 1 hour the reaction was concentrated to give a white solid. The solid was triturated with ethanol at 50° C., for 30 minutes. After cooling, filtration afforded the title compound as a white solid (90 mg, 90%). LCMS m/z 493.7 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38-1.70 (m, 12 H) 1.79 (br. s., 1 H) 2.09-2.24 (m, 1 H) 2.42 (ddd, J=13.07, 11.12, 4.68 Hz, 1 H) 3.12 (s, 3 H) 3.68-3.83 (m, 2 H) 3.87 (d, J=6.63 Hz, 2 H) 4.10 (d, J=6.44 Hz, 1 H) 6.55-6.75 (m, 2 H) 6.94-7.10 (m, 2 H) 7.61-7.80 (m, 3 H) 11.15 (br. s., 1 H)

Aufarbeitung

  1. concentrationAfter 1 hour the reaction was concentrated
  2. customto give a white solid
  3. customThe solid was triturated with ethanol at 50° C., for 30 minutes
  4. temperatureAfter cooling
  5. filtrationfiltration

Quellen und Nachweise

ORD-Eintrag
ord-93a45586e2da46c886807836594e0383
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846933B2

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