(Diethylamino)sulfur trifluoride → HCID 54576677, compound

HRID 2202802Notes

Reaction equation

HRID 2202802 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2(O)[CH2:14][CH:13]3[N:15]([C:16]([C:18]4[CH:22]=[C:21]([C:23]5[CH:24]=[N:25][NH:26][CH:27]=5)[S:20][CH:19]=4)=[O:17])[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.CCN(S(F)(F)[F:35])CC.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:8]2([F:35])[CH2:14][CH:13]3[N:15]([C:16]([C:18]4[CH:22]=[C:21]([C:23]5[CH:24]=[N:25][NH:26][CH:27]=5)[S:20][CH:19]=4)=[O:17])[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 54576247HCID 54576247, compound

Product 1

HCID 54576677HCID 54576677, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[3-(3-Chloro-pyridin-2-yl)-3-hydroxy-8-aza-bicyclo[3.2.1]oct-8-yl]-[5-(1H-pyrazol-4-yl)-thiophen-3-yl]-methanone (0.17 g, 0.41 mmol) in DCM (4 mL) was cooled to −78° C., under nitrogen, DAST (0.216 mL, 1.64 mmol) added and the reaction mixture stirred for 1 hour. Saturated aqueous sodium hydrogen carbonate and DCM were added, the organics separated, dried over sodium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 1-6% methanol/DCM. Then further purified by HPLC on a C18 cartridge, eluting with 5%-98% methanol/water with 0.1% formic acid. The fractions containing the desired product were concentrated under vacuum to give the title compound as a white solid (0.07 g). LCMS m/z 418.9 [M+H]+. R.T.=4.05/4.14 min (Analytical Method 1).

Workup

  1. dry with materialthe organics separated, dried over sodium sulphate
  2. filtrationfiltered
  3. customthe solvent removed by evaporation under vacuum
  4. customThe residue was purified by flash chromatography on silica eluting with 1-6% methanol/DCM
  5. customThen further purified by HPLC on a C18 cartridge
  6. washeluting with 5%-98% methanol/water with 0.1% formic acid
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-2d44e7afbabe467f83bf7f75078bb4e2
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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