Water → 1-[(6-Methyl-2-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

HRID 41306

Reaktionsgleichung

Reaktionsgleichung von HRID 41306
[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]=[C:60]([C:62](O)=[O:63])[CH:59]=[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]=[C:60]([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:59]=[CH:58][CH:57]=1

Komponenten

9

Edukt 6

HCID 962WaterHCID 702826-Methylpyridine-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 25545781-[4-(Trifluoromethyl)benzenesulfonyl]piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 322203661-[(6-Methyl-2-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazineAusbeute 70,4 %

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-2-pyridinecarboxylic acid (46.6 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 transferred to a separating funnel then was washed with saturated aq. 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 concentrated 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 concentrated in vacuo to yield the title compound (99 mg).

Aufarbeitung

  1. customReaction mixture
  2. customwas transferred to a 100 ml round bottom flask
  3. customtransferred to a separating funnel
  4. washthen was washed with saturated aq. 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. concentrationconcentrated to dryness in vacuo
  10. dissolutionThe residue was then dissolved in 1.8 ml 1:1 MeCN/DMSO
  11. custompurified by MDAP in 2 batches
  12. additionThe fractions containing desired product
  13. customwere combined in a 250 ml round bottom flask
  14. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-397ebc8cb4924af0af200d95dc924790
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530478B2

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