Water → HCID 21190204, compound

HRID 619531Notes

Reaction equation

HRID 619531 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:12][C:13]2[N:18]3[C:19]([C:23](OCC)=[O:24])=[C:20]([CH3:22])[N:21]=[C:17]3[CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.O>CN(C=O)C>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][N:12]2[C:13]3[N:18]4[C:17](=[N:21][C:20]([CH3:22])=[C:19]4[C:23]2=[O:24])[CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 211901605-[2-[4-(Amino)phenyl]ethan-1-ylamino]-3-ethoxycarbonyl-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 21190204HCID 21190204, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 80 mg (2.0 mmol) of 60% sodium hydride (dispension in oil) in 10 ml of DMF was added, while stirring at room temperature, 338 mg (1.0 mmol) of 5-[2-[4-(amino)phenyl]ethan-1-ylamino]-3-ethoxycarbonyl-2-methylimidazo[1,2-a]pyridine. The mixture was stirred for 30 minutes. The reaction mixture was poured into water, extracted with ethyl acetate. The extract was washed with an aqueous saline solution, dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to give 151 mg of the desired compound (51.7%, pale brown solid).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 30 minutes
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with an aqueous saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-ed9dc330a4074f62a4ccd9bc171b02d2
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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