Water → HCID 21190204, compound

HRID 1068818Notes

Reaction equation

HRID 1068818 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-78b8153d67b947d8a8323f52932168be
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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