1-[5-Nitroindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine → 1-[5-Aminoindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

HRID 2293782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2293782
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]3[C:26]([NH:27][C:28]([CH3:32])([CH3:31])[CH2:29][CH3:30])=[CH:25][CH:24]=[CH:23][N:22]=3)[CH2:17][CH2:16]1)=[O:14])=[CH:7]2)([O-])=O>CN(C)C=O.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]3[C:26]([NH:27][C:28]([CH3:31])([CH3:32])[CH2:29][CH3:30])=[CH:25][CH:24]=[CH:23][N:22]=3)[CH2:17][CH2:16]1)=[O:14])=[CH:7]2

Komponenten

4

Edukt 1

HCID 214775991-[5-Nitroindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

Produkt 1

HCID 214776001-[5-Aminoindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21901440N,N-dimethylformamide methanolLösungsmittel

Versuchsvorschrift

To a solution of 1-[5-nitroindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine (PREPARATION 67, 1.00 g) in dimethylformamide/methanol (200 ml, 50/50) under nitrogen is added palladium on carbon (10%, 250 mg). The mixture is put under hydrogen (balloon) for 4 hr and nitrogen for 17 hr, filtered through a pad of celite, and concentrated under reduced pressure to give the title compound, NMR (CDCl3) 9.25, 7.66, 7.24, 7.06, 6.88, 6.76, 6.63, 4.58, 4.05, 3.35, 3.14, 1.73, 1.35 and 0.91.

Aufarbeitung

  1. waitnitrogen for 17 hr
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cf4d9c5183d64787adeb83758cf1f546
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05686610

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