Potassium Hydroxide → HCID 22710194, compound

HRID 352926Notes

Reaction equation

HRID 352926 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[N:9][C:10]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([S:21]([C:24]4[S:28][C:27]5[CH:29]=[C:30]([C:33]#[C:34][Si](C)(C)C)[CH:31]=[CH:32][C:26]=5[CH:25]=4)(=[O:23])=[O:22])[CH2:17][CH2:16]3)=[O:14])=[N:11][CH:12]=2)=[CH:3][CH:2]=1.[OH-].[K+].[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>O1CCCC1.CO>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[CH:12]=[N:11][C:10]([C:13]([N:15]3[CH2:16][CH2:17][N:18]([S:21]([C:24]4[S:28][C:27]5[CH:29]=[C:30]([C:33]#[CH:34])[CH:31]=[CH:32][C:26]=5[CH:25]=4)(=[O:22])=[O:23])[CH2:19][CH2:20]3)=[O:14])=[N:9][CH:8]=2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 22710406HCID 22710406, compound

Product 1

HCID 22710194HCID 22710194, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixed solvent of tetrahydrofuran (5 ml) and methanol (7 ml) was dissolved 1-[[5-(4-pyridyl)pyrimidin-2-yl]carbonyl]-4-[(6-trimethylsilylethynylbenzo[b]thien-2-yl)sulfonyl]piperazine (167 mg), followed by the addition of potassium hydroxide (34 mg). The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was made weakly acidic with a saturated aqueous solution of ammonium chloride, and then made weakly alkaline with a saturated aqueous solution of sodium bicarbonate. After concentration under reduced pressure, the concentrate was extracted (4 times) with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:methanol=1:0→24:1). The resulting amorphous was dissolved in methylene chloride, followed by the dropwise addition to hexane to precipitate the resulting mixture as powder. The title compound (112 mg) was obtained as a white solid.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. extractionthe concentrate was extracted (4 times) with methylene chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column (methylene chloride:methanol=1:0→24:1)
  7. dissolutionThe resulting amorphous was dissolved in methylene chloride
  8. additionfollowed by the dropwise addition to hexane
  9. customto precipitate the resulting mixture as powder

Sources & evidence

ORD record
ord-ac7d93af7a7144c39ddf88697b8552ce
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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