Sodium hydride → HCID 13809154, compound

HRID 619523Notes

Reaction equation

HRID 619523 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:8]2[C:9]([C:13]([O:15]CC)=O)=[CH:10][CH:11]=[CH:12][C:7]2=[N:6][CH:5]=1>CN(C=O)C>[N:6]1[CH:5]=[C:4]2[NH:3][C:13](=[O:15])[C:9]3=[CH:10][CH:11]=[CH:12][C:7]=1[N:8]23

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 21190194HCID 21190194, compound

Product 1

HCID 13809154HCID 13809154, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 343 mg (8.58 mmol) of 60% sodium hydride (dispersion in oil) in 3 ml of DMF was added, while stirring at room temperature, a solution of 880 mg (4.29 mmol) of 3-amino-5-ethoxycarbonylimidazo[1,2-a]pyridine in 5 ml of DMF. The mixture was stirred for 30 minutes at 100° C. After cooling, the reaction mixture was poured into ice-water, washed with ethyl acetate. The aqueous layer was neutralized by the addition of 6N-HCl. The resulting precipitates were collected by filtration, washed with water, and dried to afford 100 mg of the desired compound (14.7%, a brown solid). The filtrate was extracted with chloroform, dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent:ethyl acetate/ethanol=10:1) to afford 27 mg of the desired compound (4.0%, a yellow solid)

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 30 minutes at 100° C
  3. temperatureAfter cooling
  4. washwashed with ethyl acetate
  5. additionThe aqueous layer was neutralized by the addition of 6N-HCl
  6. customThe resulting precipitates
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-3e5b332d3a2b4e44a6f270d990efd4da
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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