4-tert-butyl-N-[5-chloro-2-(4-nitro-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide → N-[2-(4-amino-pyrazol-1-yl)-5-chloro-pyridin-3-yl]-4-tert-butyl-benzenesulfonamide

HRID 75993

Reaktionsgleichung

Reaktionsgleichung von HRID 75993
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:16]([N:22]3[CH:26]=[C:25]([N+:27]([O-])=O)[CH:24]=[N:23]3)=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:27][C:25]1[CH:24]=[N:23][N:22]([C:16]2[C:15]([NH:14][S:11]([C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:6][CH:7]=3)(=[O:12])=[O:13])=[CH:20][C:19]([Cl:21])=[CH:18][N:17]=2)[CH:26]=1

Komponenten

4

Edukt 1

HCID 684640854-tert-butyl-N-[5-chloro-2-(4-nitro-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide

Produkt 1

HCID 59428137N-[2-(4-amino-pyrazol-1-yl)-5-chloro-pyridin-3-yl]-4-tert-butyl-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-tert-butyl-N-[5-chloro-2-(4-nitro-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide (100 mg, 0.229 mmol) in 2 mL of ethanol was added 10% Pd/C and the heterogeneous solution was stirred under an atmosphere of hydrogen. After two hours, the reaction was filtered through celite and concentrated in vacuo. The crude reside was subsequently purified by flash column chromatography (0-100% ethyl acetate in hexanes) to afford N-[2-(4-amino-pyrazol-1-yl)-5-chloro-pyridin-3-yl]-4-tert-butyl-benzene sulfonamide as a white solid: MS (ES) M+H expected 406.1, found 406.0.

Aufarbeitung

  1. filtrationthe reaction was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe crude reside was subsequently purified by flash column chromatography (0-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2741a332d9154637889f0161dc24ca93
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835468B2

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