(Diethylamino)sulfur trifluoride → HCID 68209259, compound

HRID 2202810Notes

Reaction equation

HRID 2202810 reaction equation
CCN(S(F)(F)[F:7])CC.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20](O)([C:23]2[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20]([F:7])([C:23]2[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluoride2×HCID 516892Sodium BicarbonateHCID 68877689HCID 68877689, compound

Product 1

HCID 68209259HCID 68209259, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of DAST (0.837 mL, 6.3 mmol) in DCM (20 mL) at −78° C. a solution of 3-chloro-4′-hydroxy-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (1.8 g, 5.8 mmol) in DCM (50 mL) was slowly added and allowed to warm to room temperature. Further DAST (0.6 mL) was added at 0° C. and stirred at room temperature for 30 minutes. Sodium hydrogen carbonate (sat.aq.) and DCM were added, the organics separated, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 20% ethyl acetate/cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound as a white solid (0.13 g).

Workup

  1. dry with materialthe organics separated, dried over magnesium sulphate
  2. filtrationfiltered
  3. customthe solvent removed by evaporation under vacuum
  4. customThe residue was purified by flash chromatography on silica eluting with 20% ethyl acetate/cyclohexane
  5. additionThe fractions containing the desired product
  6. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-96c0e4be75684897ab2135b3e96baa6c
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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