Cyclohexylamine → 8-cyclohexylsulfamoyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

HRID 1970013Notes

Reaction equation

HRID 1970013 reaction equation
C(N(CC)CC)C.[CH:8]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Cl[S:16]([C:19]1[CH:28]=[CH:27][C:26]2[NH:25][C:24](=[O:29])[C:23]3[NH:30][CH:31]=[C:32]([C:33]([OH:35])=[O:34])[C:22]=3[C:21]=2[CH:20]=1)(=[O:18])=[O:17]>ClCCl.CN(C)C=O>[CH:8]1([NH:14][S:16]([C:19]2[CH:28]=[CH:27][C:26]3[NH:25][C:24](=[O:29])[C:23]4[NH:30][CH:31]=[C:32]([C:33]([OH:35])=[O:34])[C:22]=4[C:21]=3[CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 685658338-cyclohexylsulfamoyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acidYield 44.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

314 μL (2.25 mmol) of triethylamine and 189 μL (1.65 mmol) of cyclohexylamine are added to 490 mg (1.5 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid suspended in 4 mL of anhydrous dichloromethane and 1 mL of anhydrous dimethylformamide. The reaction mixture is stirred for 2 days at room temperature. The solvents are evaporated, and the residue is taken up in water. The solid is filtered, rinsed with water then diisopropyl ether and dried under vacuum to give 258 mg (44%) of 8-cyclohexylsulfamoyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid in the form of a cream-coloured solid.

Workup

  1. customThe solvents are evaporated
  2. filtrationThe solid is filtered
  3. washrinsed with water
  4. dry with materialdiisopropyl ether and dried under vacuum

Sources & evidence

ORD record
ord-29990a8a1f7b4bdd86a486acfff03dd0
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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