1,1,1,3,3,3-Hexafluoro-2-(4-(4-(2-nitrophenylsulfonyl)piperazin-1-yl)phenyl)-2-propanol → 2-(4-(4-(2-Aminophenylsulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

HRID 1972536Notes

Reaction equation

HRID 1972536 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N+:30]([O-])=O)(=[O:23])=[O:22])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]>CCO.[Pd]>[NH2:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[S:21]([N:18]1[CH2:17][CH2:16][N:15]([C:12]2[CH:11]=[CH:10][C:9]([C:3]([OH:8])([C:2]([F:34])([F:33])[F:1])[C:4]([F:5])([F:6])[F:7])=[CH:14][CH:13]=2)[CH2:20][CH2:19]1)(=[O:22])=[O:23]

Participants

4

Reactant 1

HCID 866703901,1,1,3,3,3-Hexafluoro-2-(4-(4-(2-nitrophenylsulfonyl)piperazin-1-yl)phenyl)-2-propanol

Product 1

HCID 763250102-(4-(4-(2-Aminophenylsulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanolYield 65.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1,1,1,3,3,3-hexafluoro-2-(4-(4-(2-nitrophenylsulfonyl)piperazin-1-yl)phenyl)-2-propanol (0.13 g, 0.25 mmol) in EtOH (5 mL) was added 10% palladium on carbon (10 wt % (dry basis) on activated carbon, wet (water about 50%)) (0.026 g, 0.24 mmol). The reaction vessel stirred under a hydrogen atmosphere (1 atm). After 4 hours at room temperature, the reaction vessel was carefully evacuated and backfilled with N2. The solution was filtered through Celite® (diatomaceous earth) and the filtrate was concentrated onto silica. Purification by silica gel chromatography (0 to 6% MeOH in CH2Cl2) afforded 2-(4-(4-(2-aminophenylsulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (79 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.40 (s, 1H), 7.45 (d, J=8.8 Hz, 2H), 7.41 (dd, J=1.2, 8.0 Hz, 1H), 7.28-7.35 (m, 1H), 7.00 (d, J=9.0 Hz, 2H), 6.87 (d, J=8.0 Hz, 1H), 6.66 (t, J=7.2 Hz, 1H), 6.09 (s, 2H), 3.22-3.29 (m, 4H), 3.06-3.14 (m, 4H). m/z (ESI, +ve ion) 483.8 (M+H)+. GK-GKRP IC50 (Binding)=0.298 μM; GK-GKRP EC50 (LC MS/MS-2)=0.552 μM.

Workup

  1. customthe reaction vessel was carefully evacuated
  2. filtrationThe solution was filtered through Celite® (diatomaceous earth)
  3. concentrationthe filtrate was concentrated onto silica
  4. customPurification by silica gel chromatography (0 to 6% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-53b47e6652004c8c88bd97c7e46ef747
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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