Pyridine → HCID 23114764, compound

HRID 2080476Notes

Reaction equation

HRID 2080476 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(Cl)Cl.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH:19]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[C:20]2[C:25]([F:26])=[CH:24][N:23]=[C:22]([NH2:27])[CH:21]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.N1C=CC=CC=1>CCCCCC.C(OCC)(=O)C>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([S:16]([CH:19]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[C:20]2[C:25]([F:26])=[CH:24][N:23]=[C:22]([NH:27][S:2]([CH3:1])(=[O:4])=[O:3])[CH:21]=2)(=[O:17])=[O:18])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 1049Pyridine5×HCID 6344DichloromethaneHCID 31297Methanesulfonyl chloride5×HCID 23114619HCID 23114619, compound

Product 1

HCID 23114764HCID 23114764, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice cooling, methanesulfonyl chloride (12 μl, 0.157 mmol) was added to a methylene chloride (5 ml) solution of [4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-5-fluoropyridin-2-yl]amine (54 mg, 0.131 mmol) and pyridine (16 μl, 0.197 mmol). The resulting mixture was stirred at room temperature for 7 hours, followed by the addition of pyridine (16 μl, 0.197 mmol) and methanesulfonyl chloride (12 μl, 0.157 mmol). After the reaction mixture was stirred at room temperature for 17 hours, pyridine (16 μl, 0.197 mmol) and methanesulfonyl chloride (12 μl, 0.157 mmol) were added thereto. The resulting mixture was stirred at room temperature for 2 hours and then, pyridine (16 μl, 0.197 mmol) and methanesulfonyl chloride (12 μl, 0.157 mmol) were added thereto. After the resulting mixture was stirred at room temperature for 21 hours, pyridine (16 μl, 0.197 mmol) and methanesulfonyl chloride (12 μl, 0.157 mmol) were added thereto. The resulting mixture was stirred at room temperature for 2 hour and then, concentrated under reduced pressure. To the residue thus obtained was added ethyl acetate. The resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate, 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 (=2:1) eluate was concentrated under reduced pressure to give the title compound (54 mg, 0.110 mmol, 84%) as a white solid. The resulting white solid was washed with hexane-ether, and collected by filtration to afford the title compound as a white powder.

Workup

  1. stirringAfter the reaction mixture was stirred at room temperature for 17 hours
  2. stirringThe resulting mixture was stirred at room temperature for 2 hours
  3. stirringAfter the resulting mixture was stirred at room temperature for 21 hours
  4. stirringThe resulting mixture was stirred at room temperature for 2 hour
  5. concentrationconcentrated under reduced pressure
  6. customTo the residue thus obtained
  7. washThe resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customThe residue thus obtained
  12. concentrationethyl acetate (=2:1) eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1ac61328bf214347864269b13c11f781
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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