Water → (2S)-2-Methyl-1-[(6-methyl-3-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

HRID 43388

Reaktionsgleichung

Reaktionsgleichung von HRID 43388
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:3]1.CCN(C(C)C)C(C)C.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.[CH3:65][C:66]1[N:71]=[CH:70][C:69]([C:72](O)=[O:73])=[CH:68][CH:67]=1>CN(C=O)C>[CH3:1][C@H:2]1[CH2:3][N:4]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)(=[O:9])=[O:10])[CH2:5][CH2:6][N:7]1[C:72]([C:69]1[CH:70]=[N:71][C:66]([CH3:65])=[CH:67][CH:68]=1)=[O:73]

Komponenten

8

Edukt 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1378606-Methylnicotinic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59152086(S)-3-Methyl-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperazine

Produkt 1

HCID 59161381(2S)-2-Methyl-1-[(6-methyl-3-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazineAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (3S)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 2) (100 mg, 0.324 mmol) in DMF (5 ml) was added DIPEA (0.170 ml, 0.973 mmol), HOBT.H2O (49.7 mg, 0.324 mmol), HBTU (123 mg, 0.324 mmol) and 6-methyl-3-pyridinecarboxylic acid (44.5 mg, 0.324 mmol) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was evaporated in vacuo, DCM (50 ml) was added and the solution was washed with NfaHCO3 (5 ml×2). The organic layer was dried with dried magnesium sulphate which was removed by filtration and the filtrate evaporated to dryness in vacuo. The residual oil was dissolved in 1:1 MeCN/DMSO (1.8 ml) and purified by MDAP in two batches. The fractions containing the desired product were combined and evaporated to dryness in vacuo. The residue was azeotroped with toluene to remove any remaining water to yield the title compound (86 mg).

Aufarbeitung

  1. customThe reaction mixture was evaporated in vacuo, DCM (50 ml)
  2. additionwas added
  3. washthe solution was washed with NfaHCO3 (5 ml×2)
  4. dry with materialThe organic layer was dried with dried magnesium sulphate which
  5. customwas removed by filtration
  6. customthe filtrate evaporated to dryness in vacuo
  7. dissolutionThe residual oil was dissolved in 1:1 MeCN/DMSO (1.8 ml)
  8. custompurified by MDAP in two batches
  9. additionThe fractions containing the desired product
  10. customevaporated to dryness in vacuo
  11. customThe residue was azeotroped with toluene
  12. customto remove any remaining water

Quellen und Nachweise

ORD-Eintrag
ord-07cc29cb795544bf97e32eb551e92875
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536183B2

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