Ammonium formate → 2-(4-(4-((4-Amino-2-thiophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

HRID 1972508Notes

Reaction equation

HRID 1972508 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)(=[O:11])=[O:10])[S:7][CH:8]=1)([O-])=O.C([O-])=O.[NH4+]>CCO.C(Cl)Cl.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([S:9]([N:12]2[CH2:13][CH2:14][N:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([OH:33])([C:25]([F:27])([F:28])[F:26])[C:29]([F:30])([F:31])[F:32])=[CH:20][CH:19]=3)[CH2:16][CH2:17]2)(=[O:10])=[O:11])[S:7][CH:8]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 866703732-(4-(4-((4-Nitro-2-thiophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

Product 1

HCID 763141332-(4-(4-((4-Amino-2-thiophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanolYield 30.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round bottomed flask a mixture of 2-(4-(4-((4-nitro-2-thiophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (80 mg, 0.154 mmol), ammonium formate (48.6 mg, 0.770 mmol, Sigma-Aldrich, St. Louis, Mo.), and 10% Pd/C (1.639 mg, 0.015 mmol) in EtOH (10 mL) was stirring under an atmosphere of H2 (1 atm) for 18 h. Afterwards, the reaction mixture was filtered through a plug of Celite® (diatomaceous earth), and the filtrate was concentrated to give the crude product. The crude product was dissolved in CH2Cl2 and filtered through a plug of silica gel. The filtrate was concentrated to give 2-(4-(4-((4-amino-2-thiophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (23 mg).

Workup

  1. filtrationAfterwards, the reaction mixture was filtered through a plug of Celite® (diatomaceous earth)
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product
  4. filtrationfiltered through a plug of silica gel
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-12bc0b878d0344789867038b4237a120
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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