Hydrochloric Acid → HCID 22316775, compound

HRID 497173Notes

Reaction equation

HRID 497173 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.[S:15]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:29])=[O:28])=[CH:22][CH:21]=2)=[CH:16]1.C1CCN2C(=NCCC2)CC1.Cl>C(#N)C.CCN(CC)CC>[S:15]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[C:27](=[O:29])[O:28][CH2:2][C:3]=3[C:5]3[CH:6]=[CH:7][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][CH:10]=3)=[CH:24][CH:25]=2)=[CH:16]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenoneHCID 13773530HCID 13773530, compound

Product 1

HCID 22316775HCID 22316775, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 2-bromo-1-[4-(methylsulfonyl)phenyl]ethanone (0.27 g, 1 mmol) and 4-(3-thienyl)phenylacetic acid (0.19 g, 0.9 mmol) in acetonitrile (5 mL) was added Et3N (0.33 mL) at 0° C. under nitrogen. After stirring for 20 minutes at room temperature, the mixture was chilled in ice bath. DBU (0.29 mL) was added to the mixture, and stirred for 20 minutes at 0° C. To the mixture was added 1N HCl solution (8 mL) and ice-water (10 mL), and the mixture was stirred for 2 minutes. The whole was extracted with CH2Cl2 (50 mL×3), the combined organic layer washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate/hexane (1/1) followed by recrystallization from ethyl acetate/hexane to provide the title compound (0.15 g, 39% yield).

Workup

  1. temperaturethe mixture was chilled in ice bath
  2. stirringstirred for 20 minutes at 0° C
  3. stirringthe mixture was stirred for 2 minutes
  4. extractionThe whole was extracted with CH2Cl2 (50 mL×3)
  5. washthe combined organic layer washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography
  9. washeluting with ethyl acetate/hexane (1/1)
  10. customfollowed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e3dc29b204074e8786d87d8e64ca6c05
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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