Potassium Carbonate → HCID 136052393, compound

HRID 1889566Notes

Reaction equation

HRID 1889566 reaction equation
[CH2:1]([C:3]1[S:35][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]4[N:30]=[C:29](C(Cl)(Cl)Cl)[O:28][N:27]=4)=[CH:16][CH:15]=3)[C:8](=[O:12])[NH:9][C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].Br[CH2:37][C:38]1[C:42]2[CH:43]=[CH:44][C:45]([F:47])=[CH:46][C:41]=2[O:40][N:39]=1.C(=O)([O-])[O-:49].[K+].[K+]>C(#N)C>[CH2:1]([C:3]1[S:35][C:6]2[N:7]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]4[NH:30][C:29](=[O:49])[O:28][N:27]=4)=[CH:18][CH:19]=3)[C:8](=[O:12])[N:9]([CH2:37][C:38]3[C:42]4[CH:43]=[CH:44][C:45]([F:47])=[CH:46][C:41]=4[O:40][N:39]=3)[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59351731HCID 59351731, compoundHCID 675293731084628-24-9

Product 1

HCID 136052393HCID 136052393, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-ethyl-1-({2′-[5-(trichloromethyl)-1,2,4-oxadiazol-3-yl]biphenyl-4-yl}methyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.48 g), 3-(bromomethyl)-6-fluoro-1,2-benzoisoxazole (0.2 g), potassium carbonate (0.24 g) and acetonitrile (40 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 sodium hydroxide solution (4 mL) was added, and the mixture was stirred at room temperature for 1 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 residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.1 g, 19%).

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 sodium hydroxide solution (4 mL) was added
  6. stirringthe mixture was stirred at room temperature for 1 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. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-145eb6443a9b4ee18087e0a562c995e0
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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