Pyridine → HCID 23114849, compound

HRID 2080483Notes

Reaction equation

HRID 2080483 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[C:15]2[C:20]([CH3:21])=[CH:19][N:18]=[C:17]([NH2:22])[CH:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.N1C=CC=CC=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>CCCCCC.C(OCC)(=O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[C:15]2[C:20]([CH3:21])=[CH:19][N:18]=[C:17]([NH:22][S:38]([CH3:37])(=[O:40])=[O:39])[CH:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 1049Pyridine3×HCID 6344DichloromethaneHCID 31297Methanesulfonyl chloride3×HCID 23114655HCID 23114655, compound

Product 1

HCID 23114849HCID 23114849, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methylene chloride (5 ml) solution of [4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-5-methylpyridin-2-yl]amine (133 mg, 0.325 mmol) and pyridine (39 μl, 0.488 mmol) was added methanesulfonyl chloride (28 μl, 0.358 mmol) under ice cooling. The reaction mixture was stirred at room temperature for 2.5 hours. To the reaction mixture were added pyridine (26 μl, 0.325 mmol) and methanesulfonyl chloride (25 μl, 0.325 mmol). After the resulting mixture was stirred at room temperature for 16 hours, pyridine (26 μl, 0.325 mmol) and methanesulfonyl chloride (25 μl, 0.325 mmol) were added thereto. The resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure. To the residue thus obtained was added ethyl acetate. The resulting mixture was washed sequentially 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=3:2 eluate was concentrated under reduced pressure to give the title compound (108 mg, 0.222 mmol, 68%) as a white solid. The resulting white solid was washed with hexane-ether, and collected by filtration to give the title compound (67 mg) as a white powder.

Workup

  1. stirringAfter the resulting mixture was stirred at room temperature for 16 hours
  2. stirringThe resulting mixture was stirred at room temperature for 1.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customTo the residue thus obtained
  5. washThe resulting mixture was washed sequentially with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe residue thus obtained
  10. concentrationethyl acetate=3:2 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-82ef758cbb854d52968e3d86e8b691c2
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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