Hydrochloric Acid → 6'-((3,3-difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

HRID 1468075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468075
Cl.[F:2][C:3]1([F:32])[CH2:6][CH:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][C:13]2([CH2:22][CH2:21][CH:20]([O:23][CH3:24])[CH2:19][CH2:18]2)[C:12]3=[N:25]S(C(C)(C)C)=O)[CH2:4]1>O1CCOCC1.C([O-])(O)=O.[Na+]>[F:2][C:3]1([F:32])[CH2:6][CH:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15]([CH2:14][C:13]4([CH2:22][CH2:21][CH:20]([O:23][CH3:24])[CH2:19][CH2:18]4)[C:12]3=[NH:25])=[CH:16][CH:17]=2)[CH2:4]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 86706722N-(5'-((3,3-Difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide2×

Produkt 1

HCID 867067236'-((3,3-difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-imineAusbeute 116,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

HCl (4 M in 1,4-dioxane, 4.13 mL, 16.5 mmol) was added to a solution of N-(5′-((3,3-difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Intermediate 18, 750 mg, 1.65 mmol) in anhydrous 1,4-dioxane (25 mL). A white precipitate formed immediately and the resulting cloudy mixture was stirred under a nitrogen atmosphere overnight. The mixture was diluted with NaHCO3 (aq.) and extracted with DCM. The organic phase was dried and concentrated, to yield 6′-((3,3-difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2′-inden]-1′(3′H)-imine (672 mg, 1.92 mmol). The imine, trimethyl orthoformate (0.557 mL, 5.08 mmol) and 2-propanol (5 mL) was placed into a MW tube and the mixture was heated at 60° C. in an oil bath. 2-oxopropanethioamide (Intermediate 1, 397 mg, 3.85 mmol) in MeOH (15 mL) was added and the resulting mixture was stirred overnight. The mixture was concentrated in vacuo. The product was isolated using column chromatography (0-50% EtOAc in heptane) to give 106 mg (12% yield) of the title compound. MS (ES+) m/z 435 [M+H]+.

Aufarbeitung

  1. customA white precipitate formed immediately
  2. extractionextracted with DCM
  3. customThe organic phase was dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-55b30e1edd3d48d58326e4253076e6de
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000185B2

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