Hydrochloric Acid → HCID 86670430, compound

HRID 1972676Notes

Reaction equation

HRID 1972676 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)(=[O:23])=[O:22])[CH2:17][CH:16]2[CH2:29][C:30]2[CH:35]=[CH:34][N:33]=[C:32]([O:36]C)[CH:31]=2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].Cl.O1CCOCC1>C([O-])(O)=O.[Na+]>[S:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[S:21]([N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:13]=[CH:14][C:9]([C:3]([OH:8])([C:2]([F:1])([F:38])[F:39])[C:4]([F:5])([F:7])[F:6])=[CH:10][CH:11]=2)[CH:16]([CH2:29][C:30]2[CH:35]=[CH:34][NH:33][C:32](=[O:36])[CH:31]=2)[CH2:17]1)(=[O:22])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86670429HCID 86670429, compound

Product 1

HCID 86670430HCID 86670430, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

To a 100-mL round-bottomed flask was added 1,1,1,3,3,3-hexafluoro-2-(4-(2-((2-methoxy-4-pyridinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (72 mg, 0.12 mmol), 5N hydrochloric acid (0.121 mL, 0.60 mmol), and dioxane (3 mL). The reaction mixture was stirred at 100° C. for 16 h and allowed to cool to room temperature. The reaction mixture was diluted with saturated NaHCO3 (20 mL) and extracted with EtOAc (2×40 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as an off-white solid. The crude product was purified by silica gel chromatography, eluting with 5% MeOH/EtOAc to give 4-((4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-2-piperazinyl)methyl)-2(1H)-pyridinone (58 mg) as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with EtOAc (2×40 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (5 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customto give the crude material as an off-white solid
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with 5% MeOH/EtOAc

Sources & evidence

ORD record
ord-f30dcb5feeae4691ad2d0fa063b27994
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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