N,N-Dimethylethylenediamine → HCID 59725960, compound

HRID 1912808Notes

Reaction equation

HRID 1912808 reaction equation
CO[C:3]([C:5]1[C:10]2[N:11]=[CH:12][N:13]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[C:9]=2[CH:8]=[CH:7][N:6]=1)=[O:4].[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH2:27]>CO>[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH:27][C:3]([C:5]1[C:10]2[N:11]=[CH:12][N:13]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[C:9]=2[CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 59725913HCID 59725913, compound

Product 1

HCID 59725960HCID 59725960, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 5 mL of methanol, 11 mg (0.037 mmol) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine-4-carboxylic acid methyl ester prepared in Step B was dissolved, and 100 μL of N,N-dimethylethylenediamine was added thereto and the solution was refluxed under heating with stirring for two hours. The solvent was distilled under reduced pressure, and the residue was separated by Megabond Elute Silica Gel (1 g, dichloromethane:methanol=30:1 to 4:1) to obtain 7.3 mg (51%) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine-4-carboxylic acid (2-(dimethylamino)ethyl)amide as a white solid.

Workup

  1. temperaturethe solution was refluxed
  2. temperatureunder heating
  3. distillationThe solvent was distilled under reduced pressure
  4. customthe residue was separated by Megabond
  5. washElute Silica Gel (1 g, dichloromethane:methanol=30:1 to 4:1)

Sources & evidence

ORD record
ord-87276e9c0081468d8fa798c06e59d5e8
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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