Dichloromethane → N-[[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methyl]-N',N'-dimethylsulfamide

HRID 2080405Notes

Reaction equation

HRID 2080405 reaction equation
ClCCl.Cl.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH:15]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[C:16]2[N:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][CH:17]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.CN1CCOCC1.[CH3:39][N:40]([CH3:45])[S:41](Cl)(=[O:43])=[O:42]>CN(C)C1C=CN=CC=1.CCCCCC.O>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH:15]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[C:16]2[N:21]=[CH:20][C:19]([CH2:22][NH:23][S:41]([N:40]([CH3:45])[CH3:39])(=[O:43])=[O:42])=[CH:18][CH:17]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 79724-MethylmorpholineHCID 83372Dimethylsulphamoyl chlorideHCID 23114616[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine hydrochloride

Product 1

HCID 59750939N-[[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methyl]-N',N'-dimethylsulfamideYield 70%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

To a dichloromethane (5 ml) solution of the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine hydrochloride (60 mg, 0.135 mmol) obtained in Example 66 were added N-methylmorpholine (180 μl, 1.62 mmol), 4-dimethylaminopyridine (10 mg, 0.0819 mmol) and N,N-dimethylsulfamoyl chloride (66 μl, 0.609 mmol). The resulting mixture was stirred at room temperature for 24 hours. Water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed sequentially with a saturated aqueous solution of sodium bicarbonate and brine. The organic layer thus obtained was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=3:2 eluate was concentrated under reduced pressure to give the title compound (48 mg, 0.0930 mmol, 70%) as a white powder.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed sequentially with a saturated aqueous solution of sodium bicarbonate and brine
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. concentrationethyl acetate=3:2 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5db9a6f3b5274309a603e88aafb9db5a
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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