Methanol → HCID 15979330, compound

HRID 1926766Notes

Reaction equation

HRID 1926766 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][N:8]2[CH2:12][CH:11]([CH2:13][CH2:14][CH3:15])[CH2:10][C:9]2=[O:16])=[C:5]([C:17]#[N:18])[N:4]=[CH:3]1.C[OH:20]>O.[OH-].[Na+]>[CH3:1][N:2]1[C:6]([CH2:7][N:8]2[CH2:12][CH:11]([CH2:13][CH2:14][CH3:15])[CH2:10][C:9]2=[O:16])=[C:5]([C:17]([NH2:18])=[O:20])[N:4]=[CH:3]1

Participants

5

Reactant 2

HCID 887MethanolHCID 69297227HCID 69297227, compound

Product 1

HCID 15979330HCID 15979330, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

In a 25 ml, three-necked flask fitted with a magnetic stirrer, a reflux condenser and a dropping funnel under inert atmosphere, 150 mg (0.61 mmol) of 1-methyl-5-[(2-oxo-4-propylpyrrolidin-1-yl)methyl]-1H-imidazole-4-carbonitrile 122 is dissolved in MeOH (9 ml) with water (3 ml) and aqueous NaOH (35% w/w, 30 μl). The reaction mixture is refluxed 72 h, cooled down to room temperature and the solvent is evaporated to dryness. The crude reaction mixture is purified by preparative chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 96/3.6/0.4 (v/v/v/v)) and recristallized in CH2Cl2/hexane to afford 1-methyl-5-[(2-oxo-4-propylpyrrolidin-1-yl)methyl]-1H-imidazole-4-carboxamide 123 (0.07 g).

Workup

  1. temperatureThe reaction mixture is refluxed 72 h
  2. customthe solvent is evaporated to dryness
  3. customThe crude reaction mixture
  4. customis purified by preparative chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 96/3.6/0.4 (v/v/v/v))

Sources & evidence

ORD record
ord-f7cd75410be94c6b9bcaa2479e2b36a1
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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