Potassium Carbonate → HCID 136052416, compound

HRID 1889485Notes

Reaction equation

HRID 1889485 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:12]2[C:17](=[O:18])[C:16]3[CH:19]=[C:20]([CH2:22][CH3:23])[S:21][C:15]=3[NH:14][C:13]2=[O:24])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]2[N:43]=[C:42](C(Cl)(Cl)Cl)[O:41][N:40]=2)=[CH:29][CH:28]=1.C(=O)([O-])[O-:49].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:12]2[C:17](=[O:18])[C:16]3[CH:19]=[C:20]([CH2:22][CH3:23])[S:21][C:15]=3[N:14]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:39]4[NH:43][C:42](=[O:49])[O:41][N:40]=4)=[CH:29][CH:28]=3)[C:13]2=[O:24])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15290996HCID 15290996, compoundHCID 59351460HCID 59351460, compound

Product 1

HCID 136052416HCID 136052416, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 5-chloro-2-(6-ethyl-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)benzoate (0.67 g), 3-[4′-(bromomethyl)biphenyl-2-yl]-5-(trichloromethyl)-1,2,4-oxadiazole (0.96 g), potassium carbonate (0.38 g) and acetonitrile (80 mL) was stirred at 50° C. for 2 hr. Insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography and dissolved in tetrahydrofuran (10 mL) and acetone (10 mL). 1N Aqueous potassium carbonate solution (20 mL) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was adjusted to pH 5 with water and 1N hydrochloric acid, and extracted with chloroform. The obtained chloroform layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as colorless crystals (0.43 g, 38%).

Workup

  1. filtrationInsoluble material was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography
  4. dissolutiondissolved in tetrahydrofuran (10 mL)
  5. addition1N Aqueous potassium carbonate solution (20 mL) was added
  6. stirringthe mixture was stirred at room temperature for 3 hr
  7. extractionextracted with chloroform
  8. washThe obtained chloroform layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-935f1c7e8273453fb49a6639ac88468b
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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