5-(N-acetylamino)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[3,2-b]pyridine → N-[3-(1-Methylpiperidin-4-YL)-1H-pyrrolo[3,2-B]pyridin-5-YL]acetamide

HRID 581235

Reaction equation

HRID 581235 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[C:9]2[C:11]([C:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH:19]=3)=[CH:12][NH:13][C:8]2=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H][H]>[Pd].C(O)C>[C:1]([NH:4][C:5]1[N:10]=[C:9]2[C:11]([CH:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)=[CH:12][NH:13][C:8]2=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 99035405-(N-acetylamino)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[3,2-b]pyridineHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.30 gm (1.1 mMol) 5-(N-acetylamino)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[3,2-b]pyridine and 0.05 gm 10% palladium on carbon in 15 mL ethanol was hydrogenated at room temperature for 18 hours at an initial hydrogen pressure of 50 p.s.i. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with ethyl acetate containing 20% methanol and 1% ammonium hydroxide. Fractions containing product were combined and concentrated under reduced pressure to provide the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. washeluting with ethyl acetate containing 20% methanol and 1% ammonium hydroxide
  4. additionFractions containing product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d11651aed824dcbae5dfe25610cb315
Source dataset
uspto-grants-1999_07
Patent number
US05919936

Linked notes

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