Triethylamine → HCID 68584875, Verbindung

HRID 17425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17425
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]([CH3:21])[CH2:13][CH2:14][CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[O:11][C:7]=2[C:6](F)=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4]=1[CH3:29])#[N:2].C(N(CC)CC)C.[CH3:37][N:38]([CH3:44])[C@H:39]1[CH2:43][CH2:42][NH:41][CH2:40]1>CS(C)=O.ClCCl>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]([CH3:21])[CH2:13][CH2:14][CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[O:11][C:7]=2[C:6]([N:41]2[CH2:42][CH2:43][C@H:39]([N:38]([CH3:44])[CH3:37])[CH2:40]2)=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4]=1[CH3:29])#[N:2]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685844064-[{4-Cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}(methyl)amino]-N,N-dimethylbutanamide

Produkt 1

HCID 68584875HCID 68584875, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

4-[{4-Cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}(methyl)amino]-N,N-dimethylbutanamide (I-156) (0.32 g, 0.81 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (0.24 ml, 1.73 mmol) and (3S)-3-(dimethylamino)pyrrolidine (0.21 ml, 1.66 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=20:1 to 10:1), then diisopropyl ether was added and the insoluble matter was collected by filtration to obtain a colorless solid (0.22 g, 56%).

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=20:1 to 10:1)
  5. additiondiisopropyl ether was added
  6. filtrationthe insoluble matter was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-748c846b7c284a6c93517e599349c424
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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