Potassium Carbonate → HCID 60152150, compound

HRID 878989Notes

Reaction equation

HRID 878989 reaction equation
CC1C=CC=C(C)C=1C[N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](/[CH:14]=C/C(O)=O)[CH:12]=2)[CH:7]=[CH:6]1.[C:24](=[O:27])([O-])[O-:25].[K+].[K+].[Cl:30][C:31]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:32]=1[CH2:33]Cl.[OH-].[Na+].[CH3:42]N1CCCC1=O>O1CCCC1.CO>[Cl:30][C:31]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:32]=1[CH2:33][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C:24]([OH:25])=[O:27])[CH:12]=2)[C:7]([CH3:42])=[CH:6]1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 748322,6-Dichlorobenzyl chlorideHCID 68184243HCID 68184243, compound

Product 1

HCID 60152150HCID 60152150, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound obtained in the process (3) of Example 64 [64-3](272 mg) in N-methyl-2-pyrrolidone (4 mL) were added potassium carbonate (555 mg) and 2,6-dichlorobenzyl chloride (516 mg) at room temperature, and then the reaction mixture was subjected to microwave irradiation at 130° C. for 40 minutes. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give a brown oil. The obtained oil was dissolved in tetrahydrofuran (2 mL) and methanol (2 mL). 3N-sodium hydroxide (1 mL) was added at room temperature, and then the reaction mixture was subjected to microwave irradiation at 160° C. for 10 minutes. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (194 mg) as a white solid.

Workup

  1. customirradiation at 130° C. for 40 minutes
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography
  8. customto give a brown oil
  9. customirradiation at 160° C. for 10 minutes
  10. customThe reaction mixture was quenched with water
  11. extractionextracted with ethyl acetate
  12. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. concentrationthe filtrate was concentrated under reduced pressure
  15. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-795d16a68a7048a2812cc25733a9fc6c
Source dataset
uspto-grants-2015_03
Patent number
US08987473B2

Reaction notes

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