Benzenesulfonyl chloride → 1,1,1,3,3,3-hexafluoro-2-(4-((2S)-4-(phenylsulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-2-propanol

HRID 1972641Notes

Reaction equation

HRID 1972641 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH:16]2[C:21]#[C:22][CH3:23])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].C(N(CC)CC)C.[C:33]1([S:39](Cl)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(Cl)Cl>[F:25][C:2]([F:1])([F:24])[C:3]([C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:20][CH2:19][N:18]([S:39]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)(=[O:41])=[O:40])[CH2:17][C@@H:16]2[C:21]#[C:22][CH3:23])=[CH:13][CH:14]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 866704221,1,1,3,3,3-Hexafluoro-2-(4-(2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-2-propanol

Product 1

HCID 866704211,1,1,3,3,3-hexafluoro-2-(4-((2S)-4-(phenylsulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-2-propanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1,1,1,3,3,3-hexafluoro-2-(4-(2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-2-propanol (155 mg, 0.423 mmol, Example 241, Step 3) and triethylamine (302 μL, 2.17 mmol, Sigma-Aldrich, St. Louis, Mo.) in DCM (3.2 mL) was added benzenesulfonyl chloride (63.5 μL, 0.504 mmol, Sigma-Aldrich, St. Louis, Mo.) drop-wise at 0° C. The solution was stirred for 30 min and then diluted with DCM and washed with water followed by brine. The organic phase was dried over Na2SO4, filtered and concentrated. The crude residue was purified by silica gel chromatography (0 to 50% EtOAc in hexanes) to give 1,1,1,3,3,3-hexafluoro-2-(4-((2S)-4-(phenylsulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-2-propanol as a mixture of enantiomers.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica gel chromatography (0 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e1438a35aca94d4190b4cd703595bcaa
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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