Dimethylformamide → HCID 19872040, compound

HRID 35521Notes

Reaction equation

HRID 35521 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:18][N:19]([CH3:26])[C:20](=[O:25])[CH2:21][CH:22]([CH3:24])[CH3:23])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[CH3:27][N:28](C)C=O>>[CH3:26][N:19]([CH2:18][C:8]1[N:6]2[CH:7]=[C:2]([C:27]#[N:28])[CH:3]=[CH:4][C:5]2=[N:10][C:9]=1[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)[C:20](=[O:25])[CH2:21][CH:22]([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 20071492HCID 20071492, compound

Product 1

HCID 19872040HCID 19872040, compoundYield 96%

Procedure

3.7 g (0.041 mole) of cuprous cyanide and 19 g (0.041 mole) of N-{[6-iodo-2-(4-methylphenyl)imidazo[1,2-a]pyrid-3-yl]methyl}-N,3-dimethylbutanamide, prepared according to the process described in European Patent Application No. 0,172,096, are introduced into 100 ml of dimethylformamide. The mixture is heated under reflux for 4 hours and the solvent then evaporated off under reduced pressure. The residue is taken up with water and dichloromethane and the mixture treated with ammonia solution. The organic phase is washed with water and dried, and the solvent evaporated off. The residue is purified by column chromatography and taken up with pentane. 14.4 g (96%) of white solid are obtained. M.p. 151°-153° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. customthe solvent then evaporated off under reduced pressure
  4. additionthe mixture treated with ammonia solution
  5. washThe organic phase is washed with water
  6. customdried
  7. customthe solvent evaporated off
  8. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-6ad5baf129e544a1b5878cbd4f4e37a4
Source dataset
uspto-grants-1988_08
Patent number
US04767755

Reaction notes

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