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 2293782Notes

Reaction equation

HRID 2293782 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-cf4d9c5183d64787adeb83758cf1f546
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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