Potassium Carbonate → 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-methanesulfonylphenyl)piperidin-3-ol

HRID 1392412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392412
Cl.[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH:9][C:10]1([C:16]([NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH:20]2[OH:25])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:8].[CH3:26][S:27]([C:30]1(F)[CH:35]=[CH:34][CH:33]=[CH:32][CH2:31]1)(=[O:29])=[O:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH:9][C:10]1([C:16]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[S:27]([CH3:26])(=[O:29])=[O:28])[CH2:21][CH:20]2[OH:25])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:8]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 693117581-Flourophenyl methyl sulfoneHCID 693129954-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochloride

Produkt 1

HCID 693150824-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-methanesulfonylphenyl)piperidin-3-olAusbeute 51,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the solution of 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochloride (600 mg, 1.55 mmol) obtained in Step 4 and 1-flourophenyl methyl sulfone (272 g, 1.55 mmol) in 30 ml of dimethylformamide, was added potassium carbonate (500 mg). The reaction mixture was stirred overnight at about 100° C. and cooled to room temperature. The reaction mixture was diluted with 200 ml of ethyl acetate and washed with brine. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 390 mg of the titled compound as white solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. washwashed with brine
  3. customThe resulting organic layer was dried
  4. concentrationconcentrated on sodium sulfate
  5. customThe resulting residue was purified with column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f810be6e48ca426ab0b13dc524f14462
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342027B2

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