Water → 1-[(6-Methyl-3-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

HRID 43390

Reaktionsgleichung

Reaktionsgleichung von HRID 43390
[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.[CH3:55][C:56]1[N:61]=[CH:60][C:59]([C:62](O)=[O:63])=[CH:58][CH:57]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[CH3:55][C:56]1[N:61]=[CH:60][C:59]([C:62]([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:63])=[CH:58][CH:57]=1

Komponenten

9

Edukt 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1378606-Methylnicotinic acidHCID 25545781-[4-(Trifluoromethyl)benzenesulfonyl]piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 302854111-[(6-Methyl-3-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazineAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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), 6-methyl-3-pyridinecarboxylic acid (46.6 mg, 0.340 mmol) and DIPEA (0.18 ml, 1.02 mmol). The reaction mixture was stirred for 2 h 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 dried 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 (69 mg).

Aufarbeitung

  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 dried 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

Quellen und Nachweise

ORD-Eintrag
ord-39ef42d4661d4d679c3febd263139903
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536183B2

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