Pyridine → N-[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]piperidine-1-sulfonamide

HRID 2080519Notes

Reaction equation

HRID 2080519 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.[N:34]1([S:40](Cl)(=[O:42])=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.CCCCCC>C(OCC)(=O)C>[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:40]([N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)(=[O:42])=[O:41])=[N:12][CH:13]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8058HexaneHCID 11298344Piperidine-1-sulfonyl chloride2×HCID 23114671[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine

Product 1

HCID 23114834N-[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]piperidine-1-sulfonamideYield 47%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A pyridine (2 ml) solution of the [5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine (101 mg, 0.235 mmol) obtained in Example 196 and piperidine-1-sulfonyl chloride (48 mg, 0.259 mmol) was stirred at 70° C. for 19 hours. To the reaction mixture was added piperidine-1-sulfonyl chloride (48 mg, 0.259 mmol) and the resulting mixture was stirred at 70° C. for 4 days. The reaction mixture was returned to room temperature and then, concentrated under reduced pressure. The residue thus obtained was diluted with ethyl acetate. The diluted solution was washed with 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 (=4:1) eluate was concentrated under reduced pressure to yield a white solid. The resulting solid was washed with hexane-ether, and collected by filtration to give the title compound (63 mg, 0.109 mmol, 47%) as a white powder.

Workup

  1. customwas returned to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue thus obtained
  4. washThe diluted solution was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue thus obtained
  9. concentrationethyl acetate (=4:1) eluate was concentrated under reduced pressure
  10. customto yield a white solid
  11. washThe resulting solid was washed with hexane-ether
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-714ae0fd535f49fe96df0a9ae3357bee
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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