1-Hexanesulfonyl chloride → N-[(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]hexane-1-sulfonamide

HRID 384493

Reaction equation

HRID 384493 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:16])[C:14]=1[CH3:15])=[CH:11][CH:10]=[CH:9][CH:8]=2.[CH2:17]([S:23](Cl)(=[O:25])=[O:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>N1C=CC=CC=1.CN(C=O)C>[CH3:15][C:14]1[C:13](=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH2:4][NH:3][S:23]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 845041-Hexanesulfonyl chlorideHCID 685107592-(aminomethyl)-3-methylquinolin-4(1H)-one dihydrochloride

Product 1

HCID 59527425N-[(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]hexane-1-sulfonamideYield 20.5%

Reagents, catalysts & solvents 1

HCID 21954950Dimethylformamide pyridineSolvent

Procedure

To a solution of 2-(aminomethyl)-3-methylquinolin-4(1H)-one dihydrochloride (212 mg) in pyridine-DMF (8:1, 9 mL) was added hexanesulfonyl chloride (180 mg) under ice-cooling, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, and water (50 mL) was added to the residue, followed by extraction with ethyl acetate (100 mL). The organic layer was washed sequentially with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain N-[(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]hexane-1-sulfonamide (56 mg).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and water (50 mL)
  3. additionwas added to the residue
  4. extractionfollowed by extraction with ethyl acetate (100 mL)
  5. washThe organic layer was washed sequentially with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-7b5755018290426fbfa3f308eead003a
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Linked notes

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