Trifluoroacetic acid → [5-Chloro-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine

HRID 2080486Notes

Reaction equation

HRID 2080486 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([CH:27]([S:36][C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])=[CH:11][C:12]([NH:15]CC2C=CC(OC)=C(OC)C=2)=[N:13][CH:14]=1.C(=O)(O)[O-].[Na+]>CCCCCC>[Cl:8][C:9]1[C:10]([CH:27]([S:36][C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 231147075-Chloro-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridine

Product 1

HCID 23114674[5-Chloro-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]pyridin-2-yl]amineYield 77.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A trifluoroacetic acid (5 ml) solution of the 5-chloro-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridine (1.89 g, 3.45 mmol) obtained in Example 185 was stirred at 65° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. To the residue thus obtained was added a saturated aqueous solution of sodium bicarbonate, followed by extraction with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate (=2:1) eluate was concentrated under reduced pressure to yield a white solid. The resulting white solid was washed with hexane-ether, and collected by filtration to give the title compound (1.06 g, 2.67 mmol, 77%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customTo the residue thus obtained
  3. extractionfollowed by extraction with methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue thus obtained
  8. concentrationethyl acetate (=2:1) eluate was concentrated under reduced pressure
  9. customto yield a white solid
  10. washThe resulting white solid was washed with hexane-ether
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-86c18f8a3a2a44188696802e4db9d16b
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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