1,1'-Thiocarbonyldiimidazole → HCID 86633746, compound

HRID 415555Notes

Reaction equation

HRID 415555 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:9][CH:8]=[C:7]([Br:24])[CH:6]=2.[C:25](N1C=CN=C1)(N1C=CN=C1)=[S:26]>C1COCC1>[Br:24][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[C:25](=[S:26])[NH:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 802641,1'-Thiocarbonyldiimidazole2×HCID 66620332HCID 66620332, compound

Product 1

HCID 86633746HCID 86633746, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 3-[(3-amino-7-bromoquinolin-4-yl)amino]propylcarbamate (9.3 g, 23.5 mmol) and 1,1′-thiocarbonyldiimidazole (4.6 g, 26 mmol) in THF (250 mL), and the reaction mixture was heated at reflux for two hours. An analysis by liquid chromatography/mass spectrometry (LC/MS) indicated the reaction was incomplete, and additional 1,1′-thiocarbonyldiimidazole (1 g) was added. The reaction was heated at reflux for an additional hour, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was dissolved in water, and the resulting solution was extracted with tert-butyl methyl ether. The combined organic fractions were washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with a gradient of 2% ammonium hydroxide/methanol in dichloromethane) to provide 4 g of tert-butyl 3-(7-bromo-2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate.

Workup

  1. temperatureat reflux for two hours
  2. temperatureThe reaction was heated
  3. temperatureat reflux for an additional hour
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in water
  6. extractionthe resulting solution was extracted with tert-butyl methyl ether
  7. washThe combined organic fractions were washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by column chromatography on silica gel (
  12. washeluting with a gradient of 2% ammonium hydroxide/methanol in dichloromethane)

Sources & evidence

ORD record
ord-9d5e5dc61a6541c28441308151cfb3fa
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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