Water → 1-(4-Pyridinylcarbonyl)-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

HRID 41312

Reaction equation

HRID 41312 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:55]1[CH:60]=[CH:59][C:58]([C:61](O)=[O:62])=[CH:57][CH:56]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[N:55]1[CH:60]=[CH:59][C:58]([C:61]([N:15]2[CH2:16][CH2:17][N:12]([S:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:18])[F:19])=[CH:8][CH:7]=3)(=[O:10])=[O:11])[CH2:13][CH2:14]2)=[O:62])=[CH:57][CH:56]=1

Participants

9

Reactant 6

HCID 962WaterHCID 5922Isonicotinic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 25545781-[4-(Trifluoromethyl)benzenesulfonyl]piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 261817211-(4-Pyridinylcarbonyl)-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazineYield 78.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 1) (100 mg, 0.340 mmol) in DMF (5 ml) was added HOBT.H2O (52.0 mg, 0.340 mmol), HBTU (129 mg, 0.340 mmol), 4-pyridinecarboxylic acid (41.8 mg, 0.340 mmol) and DIPEA (0.178 ml, 1.019 mmol. The reaction mixture was stirred for 2 hours at room temperature. Reaction mixture was transferred to a 100 ml round bottom flask and was reduced to dryness in vacuo. The residue was dissolved in DCM (50 ml) and was transferred to a separating funnel then washed with saturated NaHCO3 solution (5 ml), twice. The organic layer was collected and dried with magnesium sulphate. The solid was removed by filtration and the filtrate collected in a 250 ml round bottom flask and reduced to dryness in vacuo. The residue was then dissolved in 1.8 ml 1:1 MeCN/DMSO and purified by MDAP in 2 batches. The fractions containing desired product were combined in a 250 ml round bottom flask and reduced in vacuo to yield the title compound (107 mg).

Workup

  1. customReaction mixture
  2. customwas transferred to a 100 ml round bottom flask
  3. customwas transferred to a separating funnel
  4. washthen washed with saturated NaHCO3 solution (5 ml)
  5. customThe organic layer was collected
  6. dry with materialdried with magnesium sulphate
  7. customThe solid was removed by filtration
  8. customthe filtrate collected in a 250 ml round bottom flask
  9. dissolutionThe residue was then dissolved in 1.8 ml 1:1 MeCN/DMSO
  10. custompurified by MDAP in 2 batches
  11. additionThe fractions containing desired product
  12. customwere combined in a 250 ml round bottom flask

Sources & evidence

ORD record
ord-041bdaa7a52e47ee8cd5283001654047
Source dataset
uspto-grants-2013_09
Patent number
US08530478B2

Linked notes

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