N-[3-(1-Methylpiperidin-4-YL)-1H-pyrrolo[3,2-B]pyridin-5-YL]acetamide → 3-(1-Methyl-piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-ylamine

HRID 398854

Reaction equation

HRID 398854 reaction equation
C([NH:4][C:5]1[N:10]=[C:9]2[C:11]([CH:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)=[CH:12][NH:13][C:8]2=[CH:7][CH:6]=1)(=O)C>Cl>[NH2:4][C:5]1[N:10]=[C:9]2[C:11]([CH:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)=[CH:12][NH:13][C:8]2=[CH:7][CH:6]=1

Participants

3

Reactant 1

HCID 10445946N-[3-(1-Methylpiperidin-4-YL)-1H-pyrrolo[3,2-B]pyridin-5-YL]acetamide

Product 1

HCID 102202303-(1-Methyl-piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-ylamineYield 93.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2.5 gm (9.2 mMol) 5-(N-acetylamino)-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine in 40 mL 2N hydrochloric acid was heated at reflux for 1 hour. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, basified (pH~11) with 2N aqueous sodium hydroxide, concentrated under reduced pressure, and extracted well with 3:1 chloroform:isopropanol. The organic extracts were combined, dried over magnesium sulfate and concentrated under reduced pressure to provide 1.98 gm (93%) of the title compound as a brown solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. concentrationconcentrated under reduced pressure
  4. concentrationconcentrated under reduced pressure
  5. extractionextracted well with 3:1 chloroform
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21cbaa88f1cd4a14bf29c9f136d7d3e9
Source dataset
uspto-grants-1998_10
Patent number
US05817671

Linked notes

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