Tetrabutylammonium Fluoride → HCID 58374830, compound

HRID 1482474Notes

Reaction equation

HRID 1482474 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C[Si]([C:23]#[C:24][C:25]1[N:30]2[N:31]=[C:32]([NH:34][C:35]([CH:37]3[CH2:39][CH2:38]3)=[O:36])[N:33]=[C:29]2[CH:28]=[CH:27][CH:26]=1)(C)C>C1COCC1.C(#N)C>[C:24]([C:25]1[N:30]2[N:31]=[C:32]([NH:34][C:35]([CH:37]3[CH2:38][CH2:39]3)=[O:36])[N:33]=[C:29]2[CH:28]=[CH:27][CH:26]=1)#[CH:23]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58374587HCID 58374587, compound

Product 1

HCID 58374830HCID 58374830, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

TBAF (0.4 mmol) 1M solution in THF is added to a solution of cyclopropanecarboxylic acid (5-trimethylsilanylethynyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide (0.32 mmol) in acetonitrile (4 mL) at room temperature. The reaction mixture is stirred at room temperature until all the starting material disappears by LCMS. The solvent of the reaction is removed under vacuum, and the mixture is redissolved in ethyl acetate. The organic phase is washed with water. The organic layer is dried over MgSO4, filtered and the solvent is removed under vacuum to afford the pure product (70 mg, 97% yield). No further purification is carried out on the product.

Workup

  1. customThe solvent of the reaction is removed under vacuum
  2. dissolutionthe mixture is redissolved in ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-641d101a2b6f4e9184175aafd07fe6e5
Source dataset
uspto-grants-2016_08
Patent number
US09415037B2

Reaction notes

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