Ethyl Acetate → 2-[5-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]propanamide

HRID 2095837Notes

Reaction equation

HRID 2095837 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.Br[CH:29]([CH3:33])[C:30]([NH2:32])=[O:31].C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12](=[N:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[N:13]([CH:29]([CH3:33])[C:30]([NH2:32])=[O:31])[CH:14]=2)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 1011182-BromopropanamideHCID 66968540N-{5-[(4-methoxybenzyl)oxy]pyridin-2-yl}-4-methylbenzenesulfonamide

Product 1

HCID 669690882-[5-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]propanamideYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{5-[(4-methoxybenzyl)oxy]pyridin-2-yl}-4-methylbenzenesulfonamide (3 g, 7.80 mmol) in N,N-dimethylformamide (30 mL) were added 2-bromopropanamide (2.82 g, 18.4 mmol) and N,N-diisopropylethylamine (4.04 mL, 23.4 mmol), and the mixture was stirred at room temperature for 2 days. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/1→ethyl acetate alone) to give the title compound (2.64 g, 74%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/1→ethyl acetate alone)

Sources & evidence

ORD record
ord-11e92ed00e504f69a840c7baaae2d02b
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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