N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide → N-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide

HRID 79591Notes

Reaction equation

HRID 79591 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][CH:21]=[C:22]([NH:23][C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[N:27][CH:26]=4)[C:15]=23)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.Cl.[Pd]>[N:11]1([C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][CH:21]=[C:22]([NH:23][C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[N:27][CH:26]=4)[C:15]=23)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 1

HCID 68760686N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide

Product 1

HCID 68763236N-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamideYield 81.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(4-(4-Benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.080 g, 0.19 mmol) was placed in MeOH (2 mL). Pd/C (0.0206 g, 0.0194 mmol) was then added, followed by the addition of 4 drops of concentrated HCl. The reaction was then placed under a balloon of H2 and stirred overnight. The reaction was filtered, washed with MeOH and concentrated to give the crude product N-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.050 g, 79.9% yield) which was used without further purification.

Workup

  1. filtrationThe reaction was filtered
  2. washwashed with MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e77a3b34e4d04362ad0aa34d9abe11a4
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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