Sodium Carbonate → (S)-tert-butyl 3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-2-oxo-1,4'-bipiperidine-1'-carboxylate

HRID 407922

Reaktionsgleichung

Reaktionsgleichung von HRID 407922
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[C:3]1=[O:21].[F:22][C:23]1[CH:28]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[C:26]([F:33])=[CH:25][C:24]=1F.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[F:22][C:23]1[CH:28]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[C:26]([F:33])=[CH:25][C:24]=1[NH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:12][CH2:13]2)[C:3]1=[O:21]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 467393961,2,4-Trifluoro-5-(methylsulfonyl)benzeneHCID 66802275(S)-tert-butyl 3-amino-2-oxo-1,4'-bipiperidine-1'-carboxylate

Produkt 1

HCID 67470435(S)-tert-butyl 3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-2-oxo-1,4'-bipiperidine-1'-carboxylateAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

(S)-tert-butyl 3-amino-2-oxo-1,4′-bipiperidine-1′-carboxylate (4.0 g, 13 mmol), 1,2,4-trifluoro-5-(methylsulfonyl)benzene (Preparation C, 4.2 g, 20 mmol) and Na2CO3 (2.9 g, 27 mmol) were dissolved in DMF (30 mL) and heated at 130° C. overnight. The reaction was concentrated and purified over silica gel (25-75% EtOAc in hexanes) to afford (S)-tert-butyl 3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-2-oxo-1,4′-bipiperidine-1′-carboxylate (4.6 g, 9.4 mmol, 70% yield) as yellow solid.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. custompurified over silica gel (25-75% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-95ac0d79b0024d8f8fdbe390394d4565
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754226B2

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