Potassium Carbonate → N-[5-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)pentyl]-2-nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamide

HRID 69002Notes

Reaction equation

HRID 69002 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)(=[O:12])=[O:11])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[N:41]([CH3:45])[C:40](=[O:46])[CH:39]=[CH:38]2>CN(C=O)C>[CH3:45][N:41]1[C:42]2[C:37](=[CH:36][C:35]([O:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][N:13]([CH2:14][CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])(=[O:11])=[O:12])=[CH:44][CH:43]=2)[CH:38]=[CH:39][C:40]1=[O:46]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 465565342-nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamideHCID 669600336-(5-bromopentyloxy)-1-methyl-1H-quinolin-2-one

Product 1

HCID 70656815N-[5-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)pentyl]-2-nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamideYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamide (308 mg), and potassium carbonate (276 mg) were added to a DMF solution (5 ml) of 6-(5-bromopentyloxy)-1-methyl-1H-quinolin-2-one (348 mg). The mixture was stirred at room temperature for 2 hours. Ice water was poured to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was washed with water, dried with anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=10:1). The purified product was condensed to dryness under reduced pressure to give 5 the title compound (535 mg) as a yellow amorphous solid.

Workup

  1. extractionfollowed by extraction
  2. washThe organic layer was washed with water
  3. dry with materialdried with anhydrous sodium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=10:1)
  5. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-695e5f44f72a429e9f9669b31b379c1f
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

Loading…