Ammonia → 4-oxo-8-(piperidin-4-ylsulfamoyl)-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-propyl carboxylate

HRID 1970015Notes

Reaction equation

HRID 1970015 reaction equation
C(N(CC)CC)C.C(OS(OCCC)(=O)=O)CC.C(OC([N:26]1[CH2:31][CH2:30][CH:29]([NH:32][S:33]([C:36]2[CH:45]=[CH:44][C:43]3[NH:42][C:41](=[O:46])[C:40]4[NH:47][CH:48]=[C:49]([C:50]([OH:52])=[O:51])[C:39]=4[C:38]=3[CH:37]=2)(=[O:35])=[O:34])[CH2:28][CH2:27]1)=O)(C)(C)C.N>CN(C)C=O.O>[O:46]=[C:41]1[C:40]2[NH:47][CH:48]=[CH:49][C:39]=2[C:38]2[CH:37]=[C:36]([S:33](=[O:35])(=[O:34])[NH:32][CH:29]3[CH2:28][CH2:27][NH:26][CH2:31][CH2:30]3)[CH:45]=[CH:44][C:43]=2[NH:42]1.[CH2:49]([C:50]([O-:52])=[O:51])[CH2:39][CH3:38]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471Triethylamine2×HCID 69015Sulfuric acid, dipropyl ester2×HCID 68936382HCID 68936382, compound

Product 1

HCID 866275254-oxo-8-(piperidin-4-ylsulfamoyl)-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-propyl carboxylateYield 67.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

107 μL (0.76 mmol) of triethylamine and 100 μL (0.61 mmol) of di-n-propylsulfate are added to a solution of 150 mg (0.3 mmol) of 8-(1-tert-butoxycarbonyl-piperidin-4-ylsulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid dissolved in 2 mL of anhydrous dimethylformamide. The solution is stirred at room temperature for 20 hours then 43 μL (0.3 mmol) of triethylamine and 51 μL (0.3 mmol) of di-n-propylsulfate are added again. Stirring is continued for a further 24 hours and 3 mL of ammonia is added. After stirring for a further 15 minutes, water is added and the product is extracted with dichloromethane. The organic phases are dried over magnesium sulfate, filtered then evaporated. The residue is dissolved in 2 mL of dichloroethane and 1 mL of trifluoroacetic acid. The solution is stirred at room temperature for 1 hour then the solvents are evaporated. The solid is taken up in dichloromethane then triethylamine is added to release the amine. The solvents are evaporated again and the residue is purified by chromatography on silica (eluent chloroform/methanol/ammonia 160/25/4) to give 44 mg (33% in two stages) of 4-oxo-8-(piperidin-4-ylsulfamoyl)-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate in the form of a white solid.

Workup

  1. stirringStirring
  2. waitis continued for a further 24 hours
  3. stirringAfter stirring for a further 15 minutes
  4. extractionthe product is extracted with dichloromethane
  5. dry with materialThe organic phases are dried over magnesium sulfate
  6. filtrationfiltered
  7. customthen evaporated
  8. dissolutionThe residue is dissolved in 2 mL of dichloroethane
  9. stirringThe solution is stirred at room temperature for 1 hour
  10. customthe solvents are evaporated
  11. additiontriethylamine is added
  12. customThe solvents are evaporated again
  13. customthe residue is purified by chromatography on silica (eluent chloroform/methanol/ammonia 160/25/4)

Sources & evidence

ORD record
ord-4d714a8693a64877b203eba81a477356
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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