Dimethyl Sulfoxide → HCID 86670958, compound

HRID 515323Notes

Reaction equation

HRID 515323 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([S:7]([C:10]2[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1.Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C(#N)C>[NH2:14][C:13]1[CH:15]=[CH:16][C:10]([S:7]([CH:4]2[CH2:3][CH2:2][N:1]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([C:25]([OH:34])([C:26]([F:27])([F:28])[F:29])[C:30]([F:31])([F:32])[F:33])=[CH:23][CH:24]=3)[CH2:6][CH2:5]2)(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 67192184HCID 67192184, compound

Product 1

HCID 86670958HCID 86670958, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(Piperidin-4-ylsulfonyl)aniline (1.748 mmol, 420 mg), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (1.748 mmol, 589 mg) and potassium carbonate (3.50 mmol, 483 mg) were combined in acetonitrile (5 mL). Dimethylsulfoxide (0.5 mL) was added and the reaction stirred at room temperature for 1.5 hours. The reaction mixture was filtered and filtrate was concentrated under vacuum. The residue was purified by SCX chromatography to give the title compound (700 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationfiltrate was concentrated under vacuum
  3. customThe residue was purified by SCX chromatography

Sources & evidence

ORD record
ord-1d5c4cd81f5e4d54a987857152e4bc07
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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