Hexane → 5-Chloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]pyridin-2-ylamine

HRID 2080535Notes

Reaction equation

HRID 2080535 reaction equation
[Cl:1][C:2]1[C:3]([CH:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])=[CH:4][C:5]([NH:8]CC2C=CC(OC)=C(OC)C=2)=[N:6][CH:7]=1.C(=O)(O)[O-].[Na+].CCCCCC>FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:3]([CH:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 516892Sodium BicarbonateHCID 231145495-Chloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridine

Product 1

HCID 587342705-Chloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]pyridin-2-ylamineYield 68%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
65 °C

Procedure

The 5-chloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridine (293 mg, 0.506 mmol) obtained in Example 295 was dissolved in trifluoroacetic acid (4 ml). The resulting solution was heated at 65° C. for 2 hours. The reaction mixture was concentrated. The residue thus obtained was basified with a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated. 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. The solid thus obtained was recrystallized from ethyl acetate-hexane to give the title compound (147 mg, 0.343 mmol, 68%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue thus obtained
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue thus obtained
  8. concentrationethyl acetate=2:1 eluate was concentrated
  9. customThe solid thus obtained
  10. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4c3fd390384b4e24b72f2d87b8270fa0
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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