Triethylsilane → HCID 67458520, compound

HRID 2389282Notes

Reaction equation

HRID 2389282 reaction equation
[ClH:1].[C:2]([C:6]1[N:7]([CH2:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:8]=[C:9]([C:11]2[CH:12]=[C:13]([C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=O)[CH:14]=[CH:15][CH:16]=2)[N:10]=1)([CH3:5])([CH3:4])[CH3:3].C([SiH](CC)CC)C.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[ClH:1].[CH2:17]([C:13]1[CH:12]=[C:11]([C:9]2[N:10]=[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[N:7]([CH2:25][CH:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:8]=2)[CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 67454366HCID 67454366, compound

Product 1

HCID 67458520HCID 67458520, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Under an argon atmosphere, a free base of Compound 48 (57 mg, 0.14 mmol) obtained in Example 48 was dissolved in trifluoroacetic acid (1 mL), and triethylsilane (91 μL, 0.57 mmol) was added thereto, and then, the mixture was stirred overnight at room temperature. Under ice-cooling, an aqueous sodium hydrogen carbonate solution was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20) to give a free base of the title compound (35 mg, 0.09 mmol, yield: 64%). Then, the obtained free base was treated with 4 mol/L hydrogen chloride-ethyl acetate to give the title compound 51 (30 mg, 0.07 mmol, yield: 78%).

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20)

Sources & evidence

ORD record
ord-30314ea611ca4603a422810a1487ef9f
Source dataset
uspto-grants-2012_09
Patent number
US08273738B2

Reaction notes

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