Pyridine → N-[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]methanesulfonamide

HRID 2080472Notes

Reaction equation

HRID 2080472 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[C:9]([CH:15]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(OCC)(=O)C>CCCCCC>[Cl:7][C:8]1[C:9]([CH:15]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])=[CH:10][C:11]([NH:14][S:35]([CH3:34])(=[O:37])=[O:36])=[N:12][CH:13]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 23114671[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine

Product 1

HCID 23114862N-[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]methanesulfonamideYield 46.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a pyridine (2 ml) solution of the [5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine (106 mg, 0.247 mmol) obtained in Example 196 was added methanesulfonyl chloride (29 μl, 0.370 mmol) under ice cooling. The resulting mixture was stirred at room temperature for 3 days and concentrated under reduced pressure. To the residue thus obtained was added ethyl acetate. The resulting mixture was washed sequentially with a saturated aqueous solution of sodium bicarbonate, water and brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure to give the title compound (58 mg, 0.114 mmol, 46%) as a white solid. The resulting white solid was washed with hexane-ether and collected by filtration to give the title compound (28 mg) as a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customTo the residue thus obtained
  3. washThe resulting mixture was washed sequentially with a saturated aqueous solution of sodium bicarbonate, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue thus obtained
  8. concentrationethyl acetate=3:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-eba54ce951d343d3b34b798aafe95549
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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