Tetrabutylammonium Fluoride → HCID 178480026, compound

HRID 69203Notes

Reaction equation

HRID 69203 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][N:20]1[CH:24]=[C:23]([C:25]2[CH:26]=[CH:27][C:28]3[N:29]([C:31]([CH:34]([C:36]4[CH:52]=[CH:51][C:39]5[N:40](COCC[Si](C)(C)C)[CH:41]=[N:42][C:38]=5[CH:37]=4)[OH:35])=[CH:32][N:33]=3)[N:30]=2)[CH:22]=[N:21]1>C1COCC1>[NH:40]1[C:39]2[CH:51]=[CH:52][C:36]([CH:34]([C:31]3[N:29]4[N:30]=[C:25]([C:23]5[CH:22]=[N:21][N:20]([CH3:19])[CH:24]=5)[CH:26]=[CH:27][C:28]4=[N:33][CH:32]=3)[OH:35])=[CH:37][C:38]=2[N:42]=[CH:41]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68640134(Rac)-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1h-benzoimidazol-5-yl]-methanol

Product 1

HCID 178480026HCID 178480026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1 M, 200 uL) was added to (rac)-[6-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-5-yl]-methanol (Stage 162.2, 42 mg, 0.088 mmol) dissolved in THF (3 ml). The reaction mixture was heated at reflux for 1 h. After evaporation of the solvent, the residue was taken into EtOAc and washed with saturated aqueous sodium carbonate. The aqueous phase was again extracted with EtOAc (3×) and combined organic layers were dried on Na2SO4. After evaporation of the solvent, the title compound was obtained as an oil (tR 0.01 min (conditions 2), MH+=346).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. customAfter evaporation of the solvent
  4. washwashed with saturated aqueous sodium carbonate
  5. extractionThe aqueous phase was again extracted with EtOAc (3×)
  6. customwere dried on Na2SO4
  7. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-554d3d8133974513be7f0c5057ed1cae
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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