Triethylamine → HCID 68585500, Verbindung

HRID 17434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17434
F[C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]([CH3:21])[C:5]([C:19]#[N:20])=[C:6]2[C:10]=1[O:9][C:8]([N:11]([CH3:18])[CH2:12][C:13]1[NH:17][N:16]=[CH:15][N:14]=1)=[N:7]2.C(N(CC)CC)C.[CH3:35][N:36]([CH3:42])[C@H:37]1[CH2:41][CH2:40][NH:39][CH2:38]1>CS(C)=O.ClCCl>[CH3:35][N:36]([CH3:42])[C@H:37]1[CH2:41][CH2:40][N:39]([C:2]2[C:3]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:4]([CH3:21])[C:5]([C:19]#[N:20])=[C:6]3[C:10]=2[O:9][C:8]([N:11]([CH3:18])[CH2:12][C:13]2[NH:17][N:16]=[CH:15][N:14]=2)=[N:7]3)[CH2:38]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685848557-fluoro-5-methyl-2-[methyl(1H-1,2,4-triazol-5-ylmethyl)amino]-6-phenyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 68585500HCID 68585500, VerbindungAusbeute 43,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

7-Fluoro-5-methyl-2-[methyl(1H-1,2,4-triazol-5-ylmethyl)amino]-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-165) (0.24 g, 0.66 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (0.19 ml, 1.37 mmol) and (3S)-3-(dimethylamino)pyrrolidine (0.17 ml, 1.34 mmol) were added, followed by stirring in a sealed tube at an external temperature of about 150° C. for 4 hours. This was diluted with dichloromethane, and washed with water and brine. After drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1), then diisopropyl ether was added and the insoluble matter was collected by filtration to obtain a beige solid (0.13 g, 42%).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. customthe solvent was evaporated away under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1)
  5. additiondiisopropyl ether was added
  6. filtrationthe insoluble matter was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-2ecd20a218244c53a42513ce737c7de1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

Notizen zur Reaktion

Wird geladen…