Acetic Acid → Irsenontrine

HRID 1043946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1043946
[OH-].[Na+].F[C:4]1[CH:9]=[C:8]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([O:17][CH3:18])[C:11]=2[CH3:19])[CH:7]=[CH:6][C:5]=1[C:20]1[N:24]([C@H:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[N:23]=[CH:22][C:21]=1[C:30]([NH2:32])=[O:31].O.C(O)(=O)C>CS(C)=O>[CH3:18][O:17][C:12]1[C:11]([CH3:19])=[C:10]([C:8]2[CH:9]=[CH:4][C:5]3[C:20]4[N:24]([C@H:25]5[CH2:29][CH2:28][O:27][CH2:26]5)[N:23]=[CH:22][C:21]=4[C:30](=[O:31])[NH:32][C:6]=3[CH:7]=2)[C:15]([CH3:16])=[CH:14][N:13]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86686376HCID 86686376, Verbindung

Produkt 1

HCID 136253996IrsenontrineAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Sodium hydroxide powder (9.43 g) was added at one time to a solution of 5-[2-fluoro-4-(2-methoxy-3,5-dimethylpyridin-4-yl)phenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxamide (37.2 g) in DMSO (186 mL) at room temperature. The reaction mixture was stirred at the same temperature for 50 minutes and then at 70° C. for 45 minutes. Under water-cooling, water (600 mL) was added dropwise to the reaction mixture, and then acetic acid (13.5 mL) was added dropwise. The precipitated powder was collected by filtration. The collected subject was washed with water and MTBE and then dried under reduced pressure to give the title compound (34.0 g).

Aufarbeitung

  1. waitat 70° C. for 45 minutes
  2. temperatureUnder water-cooling
  3. filtrationThe precipitated powder was collected by filtration
  4. washwas washed with water and MTBE
  5. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3e2eaef73b9d411badb4aefead73400f
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563565B2

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