HCID 11488045, compound → HCID 69038092, compound

HRID 2251237Notes

Reaction equation

HRID 2251237 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:30](=[O:32])[CH3:31])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[C:15]2[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:16]=2[O:25][CH:26]([CH3:28])[CH3:27])[CH2:10][CH2:9]1.[CH3:33][Li]>O1CCCC1.CCOCC>[F:1][C:2]1[CH:3]=[C:4]([C:30]([OH:32])([CH3:33])[CH3:31])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]([C:15]2[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:16]=2[O:25][CH:26]([CH3:28])[CH3:27])=[O:29])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 11488045HCID 11488045, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 69038092HCID 69038092, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.173 mmol 1-{3-Fluoro-4-[4-(2-isopropoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-phenyl}-ethanone in tetrahydrofuran (2 ml) was added dropwise 0.190 mmol 1.6M Methyllithium solution in ether at −75° C. The mixture was stirred for 2 hours and then allowed to warm to 0° C. The mixture was quenched with a 20% NH4Cl solution and extracted 3 times with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was purified on silica, eluting with dichloromethane/MeOH to yield after evaporation the title compound.

Workup

  1. customThe mixture was quenched with a 20% NH4Cl solution
  2. extractionextracted 3 times with ethyl acetate
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified on silica
  7. washeluting with dichloromethane/MeOH
  8. customto yield
  9. customafter evaporation the title compound

Sources & evidence

ORD record
ord-a7411ddf5c334e80a4d070b6c7c122de
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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