Triethylamine → HCID 86627481, compound

HRID 1969955Notes

Reaction equation

HRID 1969955 reaction equation
C(N(CC)CC)C.[CH3:8][NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl[S:19]([C:22]1[CH:31]=[CH:30][C:29]2[NH:28][C:27](=[O:32])[C:26]3[NH:33][CH:34]=[C:35]([C:36]([OH:38])=[O:37])[C:25]=3[C:24]=2[CH:23]=1)(=[O:21])=[O:20].S(Cl)(Cl)=O>ClCCl.CN(C)C=O.C(O)C>[CH3:8][N:9]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[S:19]([C:22]1[CH:31]=[CH:30][C:29]2[NH:28][C:27](=[O:32])[C:26]3[NH:33][CH:34]=[CH:35][C:25]=3[C:24]=2[CH:23]=1)(=[O:20])=[O:21].[CH2:35]([C:36]([O-:38])=[O:37])[CH3:34]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11503N-MethylbenzeneethanamineHCID 24386Thionyl ChlorideHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627481HCID 86627481, compoundYield 79.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

97 μL (0.70 mmol) of triethylamine and 61 μL (0.42 mmol) of N-methylphenethylamine are added to 115 mg (0.35 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid (synthesis 2) suspended in 2 mL of anhydrous dichloromethane and 0.5 mL of anhydrous dimethylformamide. The reaction mixture is stirred for 5 hours at room temperature. The solvents are evaporated then the residue is taken up in 2 mL of anhydrous ethanol. A solution of 255 μL (3.5 mmol) of thionyl chloride in 1 mL of anhydrous ethanol is then added slowly. The reaction mixture is stirred at 70° C. for 5 days then cooled to room temperature. The solid is filtered then the filtrate is evaporated. The residue is purified by chromatography on silica (eluent dichloromethane/methanol 96/4) to give 63 mg (40%) of 8-(methyl-phenethyl-sulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a beige solid.

Workup

  1. customThe solvents are evaporated
  2. stirringThe reaction mixture is stirred at 70° C. for 5 days
  3. temperaturethen cooled to room temperature
  4. filtrationThe solid is filtered
  5. customthe filtrate is evaporated
  6. customThe residue is purified by chromatography on silica (eluent dichloromethane/methanol 96/4)

Sources & evidence

ORD record
ord-b4c33e7b34e3404cb3fa411630181eb4
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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