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

HRID 17558
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17558
[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:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:19]([CH3:34])[C:20]([C:32]#[N:33])=[C:21]2[C:25]=1[O:24][C:23]([CH2:26][C:27]1[O:28][CH:29]=[CH:30][CH:31]=1)=[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:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:19]([CH3:34])[C:20]([C:32]#[N:33])=[C:21]3[C:25]=2[O:24][C:23]([CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)=[N:22]3)[CH2:4]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685849507-Fluoro-2-(2-furylmethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685849807-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-2-(2-furylmethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

(3S)-3-(Dimethylamino)pyrrolidine (88 μl, 0.695 mmol) and triethylamine (97 μl, 0.695 mmol) were added to a dimethyl sulfoxide (4 ml) solution of 7-fluoro-2-(2-furylmethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-271) (154 mg, 0.463 mmol), followed by stirring in an oil bath at 95° C. for 1 hour. The reaction liquid was concentrated under reduced pressure, then the residue was dissolved in ethyl acetate, and washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by silica gel column chromatography and preparative TLC (eluent, chloroform:methanol=20:1, v/v) to obtain the entitled compound (27 mg, 14%) as a pale brown foamy substance.

Aufarbeitung

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe insoluble matter was separated by filtration
  7. customthe residue obtained by concentration
  8. customwas purified by silica gel column chromatography and preparative TLC (eluent, chloroform

Quellen und Nachweise

ORD-Eintrag
ord-d984187d8e4e4fa3bd342ed862599b0b
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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