HCID 67342783, Verbindung → HCID 67343959, Verbindung

HRID 1257750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257750
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C:13]([NH:18][C:19]2[C:24]([N+:25]([O-])=O)=[CH:23][N:22]=[C:21]3[N:28]([S:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)(=[O:33])=[O:32])[CH:29]=[CH:30][C:20]=23)([CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Ni]>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C:13]([NH:18][C:19]2[C:24]([NH2:25])=[CH:23][N:22]=[C:21]3[N:28]([S:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)(=[O:33])=[O:32])[CH:29]=[CH:30][C:20]=23)([CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 1

HCID 67342783HCID 67342783, Verbindung

Produkt 1

HCID 67343959HCID 67343959, VerbindungAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-(1-Benzene sulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-3-methyl-piperidine-1-carboxylic acid benzyl ester (400 mg, 0.73 mmol) and Raney Ni (1.0 g) in ethyl acetate (20 mL) was hydrogenated at 25° C. for 1.5 hours. The mixture was filtered through Celite, thoroughly washing the filter cake with methanol. The filtrate and washings were combined and concentrated under vacuum to give about 380 mg (100%) of 3-(5-Amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-3-methyl-piperidine-1-carboxyli c acid benzyl ester without further purification. LCMS (Method J, ESI): RT=1.04 min, m+H=519.8.

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. washthoroughly washing the filter cake with methanol
  3. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c2293c3ea7eb46db831007e6516e3cd4
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461328B2

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