Sodium Bicarbonate → HCID 23114571, compound

HRID 2080484Notes

Reaction equation

HRID 2080484 reaction equation
[Cl:1][C:2]1[C:3]([CH:20]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[F:38])[S:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:4][C:5]([NH:8]CC2C=CC(OC)=C(OC)C=2)=[N:6][CH:7]=1.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:3]([CH:20]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[F:38])[S:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 23114881HCID 23114881, compound

Product 1

HCID 23114571HCID 23114571, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
65 °C

Procedure

[5-Chloro-4-[(2,5-difluorophenyl)-(4-fluorophenylsulfonyl)methyl]pyridin-2-yl](3,4-dimethoxybenzyl)amine (157 mg, 0.28 mmol) was dissolved in trifluoroacetic acid (5.0 ml). The resulting solution was stirred at 65° C. for 17 hours. After cooling, the reaction mixture was concentrated under reduced pressure. To the residue thus obtained was added a saturated aqueous solution of sodium bicarbonate. The resulting mixture was extracted with ethyl acetate. The extract was washed with brine, dried and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to give the title compound (114 mg, 99%) as a white solid.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customTo the residue thus obtained
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-5f750d910f4d431db5caa9b892e6826c
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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