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Triethylamine → 5-methyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-(2-nitrophenyl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17502
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17502
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.F[C:17]1[C:18]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[C:19]([CH3:37])[C:20]([C:35]#[N:36])=[C:21]2[C:25]=1[O:24][C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N+:32]([O-:34])=[O:33])=[N:22]2>CS(C)=O>[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][N:5]([C:17]2[C:18]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[C:19]([CH3:37])[C:20]([C:35]#[N:36])=[C:21]3[C:25]=2[O:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])=[N:22]3)[CH2:4]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685846847-Fluoro-5-methyl-2-(2-nitrophenyl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685855645-methyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-(2-nitrophenyl)-6-phenyl-1,3-benzoxazole-4-carbonitrileAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(3S)-3-(Dimethylamino)pyrrolidine (90 μl, 0.71 mmol) and triethylamine (200 μl) were added to a dimethyl sulfoxide (5 ml) solution of 7-fluoro-5-methyl-2-(2-nitrophenyl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-210) (204 mg, 0.55 mmol). The system was purged with nitrogen, then sealed up, and heated at 100° C. for 1.5 hours. After cooling, the solvent was evaporated away under reduced pressure, then the resulting residue was dissolved in chloroform, and washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated away under reduced pressure, and the resulting residue was subjected to silica gel column chromatography. Elution with a mixed solvent of chloroform/methanol (98:2, v/v) gave a main product. This was washed with a mixed solvent of isopropyl ether and ethanol, and the solid was collected by filtration to obtain the entitled compound (137 mg, 54%) as a yellow solid.

Aufarbeitung

  1. customThe system was purged with nitrogen
  2. customsealed up
  3. temperatureAfter cooling
  4. customthe solvent was evaporated away under reduced pressure
  5. dissolutionthe resulting residue was dissolved in chloroform
  6. washwashed with water and saturated brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated away under reduced pressure
  9. washElution with a mixed solvent of chloroform/methanol (98:2
  10. customv/v) gave a main product
  11. washThis was washed with a mixed solvent of isopropyl ether and ethanol
  12. filtrationthe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-a12808ff5e0b4569a74f1f648932b6d4
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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