(Diethylamino)sulfur trifluoride → HCID 54577107, compound

HRID 2202803Notes

Reaction equation

HRID 2202803 reaction equation
O[C:2]1([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[CH2:8][CH:7]2[N:9]([C:10]([C:12]3[CH:16]=[C:15]([C:17]4[CH:18]=[N:19][NH:20][CH:21]=4)[S:14][CH:13]=3)=[O:11])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.CCN(S(F)(F)[F:33])CC.C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:33][C:2]1([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[CH2:8][CH:7]2[N:9]([C:10]([C:12]3[CH:16]=[C:15]([C:17]4[CH:18]=[N:19][NH:20][CH:21]=4)[S:14][CH:13]=3)=[O:11])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 54577105HCID 54577105, compound

Product 1

HCID 54577107HCID 54577107, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(3-Hydroxy-3-thiazol-2-yl-8-aza-bicyclo[3.2.1]oct-8-yl)-[5-(1H-pyrazol-4-yl)-thiophen-3-yl]-methanone (0.09 g, 0.23 mmol) in DCM (30 mL) was cooled to −78° C., under nitrogen. DAST (0.04 mL, 0.3 mmol) was added and the reaction mixture stirred for 1 hour. Saturated aqueous sodium hydrogen carbonate and DCM were added, the organics separated, washed with brine, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residues were purified by flash chromatography, eluting with ethyl acetate. The fraction containing the desired product was concentrated under vacuum to give the title compound as a white solid (0.012 g). LCMS m/z 389.1 [M+H]+. R.T.=8.05 min (Analytical Method 2).

Workup

  1. washthe organics separated, washed with brine
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation under vacuum
  5. customThe residues were purified by flash chromatography
  6. washeluting with ethyl acetate
  7. additionThe fraction containing the desired product
  8. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-5acc1c2e4c50480ea049995eaafd5e95
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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