Stannous chloride dihydrate → Methyl 1-(4-(3-amino-6-bromoquinolin-4-ylamino)-2-(trifluoromethyl)phenyl)piperidine-4-carboxylate

HRID 336888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336888
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-])=O)=[C:5]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][CH:25]([C:28]([O:30][CH3:31])=[O:29])[CH2:24][CH2:23]2)=[C:18]([C:32]([F:35])([F:34])[F:33])[CH:17]=1.O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[NH2:12][C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH2:23][CH2:24][CH:25]([C:28]([O:30][CH3:31])=[O:29])[CH2:26][CH2:27]3)=[C:18]([C:32]([F:33])([F:35])[F:34])[CH:17]=1)=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2

Komponenten

5

Edukt 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 67008148Methyl 1-(4-(6-bromo-3-nitroquinolin-4-ylamino)-2-(trifluoromethyl)phenyl)piperidine-4-carboxylate

Produkt 1

HCID 67008348Methyl 1-(4-(3-amino-6-bromoquinolin-4-ylamino)-2-(trifluoromethyl)phenyl)piperidine-4-carboxylateAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of compound 8.2 methyl 1-(4-(6-bromo-3-nitroquinolin-4-ylamino)-2-(trifluoromethyl)phenyl)piperidine-4-carboxylate (0.26 g, 0.47 mmol, 1 equiv.) in dioxane (3 mL) at room temperature was added Tin(II) chloride dihydrate (0.53 g, 2.35 mmol, 5 equiv.). The resulting mixture was heated to 80° C. under argon for 5 hours. Upon cooling to room temperature, the mixture was neutralized with aqueous NaHCO3 and filtered. The flitrate was extrated with EtOAc (30 mL×2) and the combined organic layer was washed with water (50 mL) and brine (50 mL). The organic phase was dried over Na2SO4. After removal of solvent under vacuum, the resulting residue was purified via flash chromatography (hexanes:EtOAc 1:1) to afford desired product 8.3 methyl 1-(4-(3-amino-6-bromoquinolin-4-ylamino)-2-(trifluoromethyl)phenyl)piperidine-4-carboxylate (0.18 g; 73%). LC-MS (M+H): 523.10

Aufarbeitung

  1. temperatureUpon cooling to room temperature
  2. filtrationfiltered
  3. washthe combined organic layer was washed with water (50 mL) and brine (50 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customAfter removal of solvent under vacuum
  6. customthe resulting residue was purified via flash chromatography (hexanes:EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-1b623228fb084badb3f91f2787b63b19
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889706B2

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