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 502815

Reaktionsgleichung

Reaktionsgleichung von HRID 502815
[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-1e6a9e0b699a475f97b5fdf398b39eac
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776877B2

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