Imidazole → HCID 13505203, compound

HRID 1731744Notes

Reaction equation

HRID 1731744 reaction equation
N1C=CN=C1.S(Cl)(Cl)=O.[CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:17]=[C:18]3[C:26](=[CH:27][CH:28]=2)[NH:25][C:24]2[CH:23]=[N:22][C:21]([C:29](O)=[O:30])=[C:20]([CH3:32])[C:19]3=2)[CH2:12][CH:11]=1.[C:33](=[N:37]O)([NH2:36])[CH2:34][CH3:35]>O1CCCC1.CN(C)C=O>[CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:17]=[C:18]3[C:26](=[CH:27][CH:28]=2)[NH:25][C:24]2[CH:23]=[N:22][C:21]([C:29]4[O:30][N:37]=[C:33]([CH2:34][CH3:35])[N:36]=4)=[C:20]([CH3:32])[C:19]3=2)[CH2:12][CH:11]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 4092053N-HydroxypropionimidamideHCID 13505189HCID 13505189, compound

Product 1

HCID 13505203HCID 13505203, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.36 g (20 mmol) of imidazole is combined in 15 ml of absolute tetrahydrofuran with 0.36 ml of thionyl chloride in 5 ml of absolute tetrahydrofuran. After 15 minutes of agitation at room temperature, the mixture is suctioned off from the precipitate. The filtrate is added to a solution of 0.33 g (1.08 mmol) of 6-(1-cyclohexen-4-yl)-4-methyl-β-carboline-3-carboxylic acid in 15 ml of absolute dimethylformamide. After agitation for one hour at room temperature, the mixture is combined with 1.15 g (13 mmol) of propionamidoxime, the tetrahydrofuran is distilled off, and the reaction solution is heated for 3 hours under reflux. After the solvent has been removed by distillation, the mixture is distributed in methylene chloride/saturated sodium bicarbonate solution, the organic phase is washed with saturated sodium chloride solution until it is neutral, dried over magnesium sulfate, filtered, and concentrated to dryness. After column chromatography over silica gel with methylene chloride:ethanol=10:1 as the eluent, and recrystallization from ethanol/hexane, the residue yields 194 mg (50% of theory) of 6-(1-cyclohexen-4-yl)-4-methyl-3-(3-ethyl-1,2,4-oxadiazol-5-yl)-β-carboline, mp 247°-248° C.

Workup

  1. waitAfter agitation for one hour at room temperature
  2. distillationthe tetrahydrofuran is distilled off
  3. temperaturethe reaction solution is heated for 3 hours
  4. temperatureunder reflux
  5. customAfter the solvent has been removed by distillation
  6. washthe organic phase is washed with saturated sodium chloride solution until it
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customAfter column chromatography over silica gel with methylene chloride:ethanol=10:1 as the eluent, and recrystallization from ethanol/hexane

Sources & evidence

ORD record
ord-ef040ed4b6b7448895d294490780c0aa
Source dataset
uspto-grants-1986_11
Patent number
US04623649

Reaction notes

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