Tetrabutylammonium Fluoride → HCID 59320886, compound

HRID 341224Notes

Reaction equation

HRID 341224 reaction equation
[F:1][C:2]([F:30])([F:29])[CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[N:18]3[CH:19]=[CH:20][C:21]([C:23]#[C:24][Si](C)(C)C)=[CH:22][C:17]3=[N:16][CH:15]=2)[CH:9]=1)=[O:6].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[C:23]([C:21]1[CH:20]=[CH:19][N:18]2[C:14]([C:10]3[CH:9]=[C:8]([NH:7][C:5]([NH:4][CH2:3][C:2]([F:30])([F:29])[F:1])=[O:6])[CH:13]=[CH:12][CH:11]=3)=[CH:15][N:16]=[C:17]2[CH:22]=1)#[CH:24]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59320861HCID 59320861, compound

Product 1

HCID 59320886HCID 59320886, compoundYield 19.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2,2,2-Trifluoro-ethyl)-3-[3-(7-trimethylsilanylethynyl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-urea (25 mg, 0.06 mmol) in THF (5 ml) at 0° C. was added a 1M tetrabutylammonium fluoride solution (0.09 ml) and the reaction mixture stirred for 1 h at 0° C. The reaction mixture was diluted with water and extracted with CH2Cl2. The organic layer was washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by reverse phase HPLC to afford the product as an off-white solid (4.2 mg). MS: [M+H]+ 359

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d74a6e7e475245cdb83b51ca8d239411
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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