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

HRID 79600Notes

Reaction equation

HRID 79600 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:26])[CH3:25])[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:26])[CH3:25])[C:15]=23)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 1

HCID 68758316N-(4-(4-Benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide

Product 1

HCID 68761313N-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamideYield 98.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(4-(4-Benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide (0.150 g, 0.429 mmol) was placed in MeOH (3 mL). Pd/C (0.0914 g, 0.0429 mmol) was then added, followed by the addition of 3 drops of concentrated HCl. The reaction was then placed under a H2 balloon for 3 hours. The reaction was then filtered, but the product was insoluble. The solids were slurried with 1:1 MeOH:THF (5×) and filtered. The filtrate was then concentrated to give the crude product N-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide (0.110 g, 77.1% yield), which was used without further purification.

Workup

  1. customfor 3 hours
  2. filtrationThe reaction was then filtered
  3. filtrationTHF (5×) and filtered
  4. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-fccea1e1981b491d9401b1db02f87768
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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