Tetrabutylammonium Fluoride → HCID 178474062, compound

HRID 537077Notes

Reaction equation

HRID 537077 reaction equation
[O:1]=[S:2]1(=[O:36])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[N:8]=[C:9]([C:25]2[C:30]([CH3:31])=[CH:29][N:28]=[C:27]([NH:32][C:33](=[O:35])[CH3:34])[CH:26]=2)[O:10][C:11]=1[C:12]1[N:16]=[CH:15][N:14](COCC[Si](C)(C)C)[N:13]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[O:36]=[S:2]1(=[O:1])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[N:8]=[C:9]([C:25]2[C:30]([CH3:31])=[CH:29][N:28]=[C:27]([NH:32][C:33](=[O:35])[CH3:34])[CH:26]=2)[O:10][C:11]=1[C:12]1[NH:16][CH:15]=[N:14][N:13]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66748949HCID 66748949, compound

Product 1

HCID 178474062HCID 178474062, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-{4-[4-(1,1-dioxidoisothiazolidin-2-yl)-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (from the previous step) in THF (10 mL) was added TBAF in THF (1M, 3.3 mL). The reaction mixture was allowed to stir at rt overnight. The mixture was concentrated to dryness and then diluted with EtOAc. The mixture was washed with water. The organic solution was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N-{4-[4-(1,1-dioxidoisothiazolidin-2-yl)-5-(4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (Compound I-50) (0.028 g, 12%). LCMS (FA): m/z=404.6 (M+H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additiondiluted with EtOAc
  3. washThe mixture was washed with water
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-30534d1744de4cd287b8e2beea748977
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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