Sodium Hydroxide → 6-Aminomethyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amide

HRID 2080774Notes

Reaction equation

HRID 2080774 reaction equation
[CH2:1]([N:4]([CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][N:15]2[CH:22]=1)=[O:11])[CH2:2][CH3:3].[OH-].[Na+]>[Ni].C(O)C>[CH2:23]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]2[CH2:19][CH2:18][CH:17]([CH2:20][NH2:21])[CH2:16][N:15]2[CH:22]=1)=[O:11])[CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 231554976-Cyano-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amide

Product 1

HCID 231556046-Aminomethyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amideYield 97.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

An ethanol solution (20 ml) containing the compound (40.2 mg) obtained in Example 19-2 was added with an ethanol suspension of Raney nickel and a 1 mol/l sodium hydroxide aqueous solution (2.0 ml), and the whole was stirred at room temperature for 14 hours under a hydrogen atmosphere. The catalyst was removed by filtration through Celite. The residue obtained by distilling the solvent off under reduced pressure was dissolved in chloroform, washed with water and a saturated saline solution, and dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (40.1 mg) as a yellow oily substance.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customThe residue obtained
  3. distillationby distilling the solvent off under reduced pressure
  4. dissolutionwas dissolved in chloroform
  5. washwashed with water
  6. dry with materiala saturated saline solution, and dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-d0fe42e535094553a9f944ac1626497c
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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