4-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]butanenitrile → 5-(4-Aminobutyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 629927Notes

Reaction equation

HRID 629927 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([CH2:13][CH2:14][CH2:15][C:16]#[N:17])=[CH:10][CH:11]=2)[N:6]([CH3:18])[C:5]1=[O:19]>[Ni].C(O)C>[NH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:9]1[N:8]=[C:7]2[N:6]([CH3:18])[C:5](=[O:19])[N:4]([CH2:3][C:2]([CH3:1])([CH3:20])[CH3:21])[C:12]2=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 711367894-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]butanenitrile

Product 1

HCID 711367765-(4-Aminobutyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

To a mixture of Raney nickel (1 mL) in ethanol 2M NH3 solution (5 mL) under nitrogen was added 38-1 (0.40 g, 1.40 mmol) dissolved in ethanol (1 mL). The mixture was flushed with hydrogen and stirred overnight under a hydrogen filled balloon. The solution was filtered through a syringe and the filtrate was concentrated to give 38-2. (0.41 g, 100%). LRMS (ES) (M+H)+: observed=291.2, calculated=291.4.

Workup

  1. customThe mixture was flushed with hydrogen
  2. filtrationThe solution was filtered through a syringe
  3. concentrationthe filtrate was concentrated
  4. customto give 38-2

Sources & evidence

ORD record
ord-0e439daacd144b7c82de2b79f9abdbf1
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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