(Diethylamino)sulfur trifluoride → HCID 17972412, compound

HRID 475511Notes

Reaction equation

HRID 475511 reaction equation
[CH2:1]([N:8]1[C:12]2[CH2:13][CH:14](O)[CH2:15][C:11]=2[C:10]([C:17]#[N:18])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(S(F)(F)[F:25])CC>ClCCl.C(OCC)(=O)C>[CH2:1]([N:8]1[C:12]2[CH2:13][CH:14]([F:25])[CH2:15][C:11]=2[C:10]([C:17]#[N:18])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 23135152HCID 23135152, compound

Product 1

HCID 17972412HCID 17972412, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-benzyl-5-hydroxy-1,4,5,6-tetrahydrocyclo-penta[c]pyrazole-3-carbonitrile (see Example 9.7, 30 mg, 0.125 mmol) in anhydrous dichloromethane (0.9 mL) was added DAST (33 μL, 0.25 mmol) under a nitrogen atmosphere. After stirring at room temperature for 15 minutes, the reaction mixture was diluted with ethyl acetate, washed with saturated NaHCO3 solution and brine. The organic layer was dried over anhydrous Na2SO4 filtered and concentrated in vacuo. The residue was purified by PTLC (SiO2) using 30% ethyl acetate-hexanes to give the desired compound (16 mg).

Workup

  1. washwashed with saturated NaHCO3 solution and brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by PTLC (SiO2)

Sources & evidence

ORD record
ord-d70ced536abd48d4b19444fdc69e8b68
Source dataset
uspto-grants-2014_01
Patent number
US08637555B2

Reaction notes

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