Sodium Iodide → N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-2-nitro-N-{2-[4-(pyridin-3-ylmethoxy)piperidin-1-yl]ethyl}benzenesulfonamide

HRID 69018Notes

Reaction equation

HRID 69018 reaction equation
[I-].[Na+].[CH3:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][N:18]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N+:35]([O-:37])=[O:36])(=[O:28])=[O:27])[CH2:19][CH2:20]OS(C)(=O)=O)=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]1=[O:38].[N:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][O:46][CH:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)[CH:40]=1.C(N(C(C)C)C(C)C)C>C(#N)C>[CH3:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:19][CH2:20][N:50]3[CH2:51][CH2:52][CH:47]([O:46][CH2:45][C:41]4[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=4)[CH2:48][CH2:49]3)[S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N+:35]([O-:37])=[O:36])(=[O:27])=[O:28])=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]1=[O:38]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 207352943-((4-Piperidinyloxy)methyl)pyridineHCID 86762687Methanesulfonic acid 2-[[3-(1-methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)propyl]-(2-nitro-benzenesulfonyl)amino]-ethyl ester

Product 1

HCID 86762686N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-2-nitro-N-{2-[4-(pyridin-3-ylmethoxy)piperidin-1-yl]ethyl}benzenesulfonamideYield 67.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Sodium iodide (2.93 g) was added to a acetonitrile solution (20 ml) of methanesulfonic acid 2-[[3-(1-methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)propyl]-(2-nitro-benzenesulfonyl)amino]-ethyl ester (4.37 g), and stirred at 60° C. for 1 hours. The reaction mixture was cooled to room temperature. 4-(pyridin-3-ylmethoxy)piperidine (1.87 g) and N-ethyl diisopropylamine (4.23 ml) were then added to the reaction mixture and stirred at 60° C. for 5 hours. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. Water was added to the residue, and extraction with dichloromethane was performed. The organic layer was washed with water, and a saturated sodium chloride aqueous solution, in this order. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1). The purified product was concentrated under reduced pressure to give the title compound (3.48 g) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringstirred at 60° C. for 5 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionWater was added to the residue, and extraction with dichloromethane
  6. washThe organic layer was washed with water
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1)
  10. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-adec4ad213f84804b11f908c30e5982f
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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