Water → Mubritinib

HRID 352055

Reaktionsgleichung

Reaktionsgleichung von HRID 352055
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.Cl[CH2:18][C:19]1[N:20]=[C:21](/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[O:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.CO>[F:35][C:32]([F:33])([F:34])[C:29]1[CH:30]=[CH:31][C:26](/[CH:25]=[CH:24]/[C:21]2[O:22][CH:23]=[C:19]([CH2:18][O:16][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[N:2]4)=[CH:15][CH:14]=3)[N:20]=2)=[CH:27][CH:28]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 9857126HCID 9857126, VerbindungHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenol2×

Produkt 1

HCID 6444692MubritinibAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

4-[4-(1H-1,2,3-Triazol-1-yl)butyl]phenol (400 mg, 1.84 mmol) and 4-(chloromethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (529 mg, 1.84 mmol) were dissolved in dimethylformamide (3 ml) and potassium carbonate (279 mg, 2.02 mmol) was added. The mixture was stirred at 65-75° C. for 4 hours. 4-[4-(1H-1,2,3-Triazol-1-yl)butyl]phenol (40 mg, 0.184 mmol) was added and the mixture was stirred at 65-75° C. for further 3 hours. The mixture was cooled to room temperature and water (5 ml) was added, then methanol (3 ml) was added. The mixture was stirred at room temperature for 40 min, and the precipitated crystals were collected by filtration and washed with water. The crystals were dried under reduced pressure to give 1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-1,2,3-triazole (799 mg, yield 93%).

Aufarbeitung

  1. stirringthe mixture was stirred at 65-75° C. for further 3 hours
  2. temperatureThe mixture was cooled to room temperature
  3. stirringThe mixture was stirred at room temperature for 40 min
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with water
  6. customThe crystals were dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-48ba846d4d674c9ab2d6e54c1c312e97
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743924B2

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