Cesium carbonate → HCID 10003944, compound

HRID 1716330Notes

Reaction equation

HRID 1716330 reaction equation
Cl[C:2]1[N:6](C2CCCCO2)[C:5]2[CH:13]=[C:14]([Cl:18])[C:15]([Cl:17])=[CH:16][C:4]=2[N:3]=1.Cl.[CH3:20][S:21]([N:24]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:26]2([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH2:25]1)(=[O:23])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>O1CCOCC1.O>[Cl:17][C:15]1[C:14]([Cl:18])=[CH:13][C:5]2[N:6]=[C:2]([N:29]3[CH2:30][CH2:31][C:26]4([C:32]5[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=5)[N:24]([S:21]([CH3:20])(=[O:22])=[O:23])[CH2:25]4)[CH2:27][CH2:28]3)[NH:3][C:4]=2[CH:16]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 21956075HCID 21956075, compoundHCID 219560841-(Methylsulfonyl)spiro[indoline-3,4'-piperidine] hydrochloride

Product 1

HCID 10003944HCID 10003944, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2,5,6-trichloro-N-tetrahydropyranyl-benzimidazole (213 mg, 0.70 mmol) and 1-methylsulfonylspiro[indoline-3,4′-piperidine]hydrochloride (168 mg, 0.56 mmol) in dioxane (10 mL) was added cesium carbonate (562 mg, 0.47 mmol). The mixture was stirred at 150° C. for 14 hours in a sealed tube and then cooled. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated in vacuo. The resulting residue was dissolved in methanol (10 mL), and camphor sulfonic acid (100 mg, 0.70 mmol) was added thereto, then stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo, and the residue was neutralized with 0.1M aqueous sodium hydroxide, then extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The precipitate formed upon addition of ethyl acetate to the residue was collected by filtration and dried to give the title compound (86 mg, 34%).

Workup

  1. temperaturecooled
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting residue was dissolved in methanol (10 mL)
  6. stirringstirred at room temperature for 12 hours
  7. concentrationThe reaction mixture was concentrated in vacuo
  8. extractionextracted with chloroform
  9. washThe organic layer was washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe precipitate formed upon addition of ethyl acetate to the residue
  13. filtrationwas collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-e3230498421748cdb56fbaa46fa3c822
Source dataset
uspto-grants-2010_09
Patent number
US07803807B2

Reaction notes

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