Sodium hydride → HCID 21190144, compound

HRID 1068814Notes

Reaction equation

HRID 1068814 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:8]2[C:9]([C:13](OCC)=[O:14])=[CH:10][CH:11]=[CH:12][C:7]2=[N:6][C:5]=1[CH3:18]>CN(C=O)C>[CH3:18][C:5]1[N:6]=[C:7]2[N:8]3[C:4]=1[NH:3][C:13](=[O:14])[C:9]3=[CH:10][CH:11]=[CH:12]2

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 21190179HCID 21190179, compound

Product 1

HCID 21190144HCID 21190144, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 610 mg (15.3 mmol) of 60% sodium hydride (dispersion in oil) in 5 ml of DMF was added, while stirring at room temperature, a solution of 1.67 g (7.62 mmol) of 3-amino-5-ethoxycarbonyl-2-methyl-imidazo[1,2-a]pyridine in 5 ml of DMF. The mixture was stirred for 10 minutes, then for 30 minutes at 100° C. After cooling, the reaction mixture was poured into ice-water, and washed with chloroform. To the aqueous layer was added 6N-HCl to adjust the pH to 5-6. The resulting precipitates were collected by filtration, washed with water and diethyl ether, successively, and dried to afford 357 mg of the desired compound (27.0%, a brown solid).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 10 minutes
  3. temperatureAfter cooling
  4. washwashed with chloroform
  5. additionTo the aqueous layer was added 6N-HCl
  6. customThe resulting precipitates
  7. filtrationwere collected by filtration
  8. washwashed with water and diethyl ether
  9. customsuccessively, and dried

Sources & evidence

ORD record
ord-0b5ac07ddacd426c97dc8bce07c2ccda
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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