Dimethylformamide → 2-[1-(5-Ethyl-pyrimidin-2-yl)-piperidin-4-yl]-5-(2-fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridine

HRID 1471788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1471788
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[CH:20]=[C:19]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[O:18][C:15]2=[CH:16][N:17]=1.Cl[C:28]1[N:33]=[CH:32][C:31]([CH2:34][CH3:35])=[CH:30][N:29]=1.C(N(CC)C(C)C)(C)C.CN(C)C=O>O>[CH2:34]([C:31]1[CH:30]=[N:29][C:28]([N:24]2[CH2:25][CH2:26][CH:21]([C:19]3[O:18][C:15]4=[CH:16][N:17]=[C:12]([C:3]5[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=5[F:1])[CH:13]=[C:14]4[CH:20]=3)[CH2:22][CH2:23]2)=[N:33][CH:32]=1)[CH3:35]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 866945755-(2-Fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine

Produkt 1

HCID 717367202-[1-(5-Ethyl-pyrimidin-2-yl)-piperidin-4-yl]-5-(2-fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5-(2-fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine (70 mg), 2-chloro-5-ethyl-pyrimidine (25 mg), N,N-diisopropyl-ethylamine (67 μL), and N,N-dimethylformamide (1 mL) is stirred at 120° C. for 4 h and then at 100° C. overnight. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1) to give the title compound. LC (method 1): tR=1.18 min; Mass spectrum (ESI+): m/z=481 [M+H]+.

Aufarbeitung

  1. customat 100° C.
  2. customovernight
  3. temperatureAfter cooling to room temperature
  4. extractionthe resulting mixture is extracted with ethyl acetate
  5. washThe combined extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0bfd503cdfcd4477812882eb938be839
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012456B2

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