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Triethylamine → HCID 68584869, Verbindung

HRID 17460
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17460
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:17]#[N:18])[C:10]([CH3:16])=[C:11]([CH2:14][CH3:15])[C:12]=3F)[N:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:26][N:27]([CH3:33])[C@H:28]1[CH2:32][CH2:31][NH:30][CH2:29]1.C(=O)([O-])O.[Na+]>CS(C)=O.C(OCC)(=O)C>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:17]#[N:18])[C:10]([CH3:16])=[C:11]([CH2:14][CH3:15])[C:12]=3[N:30]3[CH2:31][CH2:32][C@H:28]([N:27]([CH3:33])[CH3:26])[CH2:29]3)[N:8]=2)[CH2:3][CH2:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 68584694HCID 68584694, Verbindung

Produkt 1

HCID 68584869HCID 68584869, VerbindungAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-Cyclopropyl-6-ethyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-181) (108 mg, 0.44 mmol) was dissolved in dimethyl sulfoxide (3 ml), then at room temperature, triethylamine (93 μl, 0.66 mmol) and (3S)-3-(dimethylamino)pyrrolidine (73 μl, 0.57 mmol) were added. The solution was stirred under nitrogen atmosphere at 90° C. for 13 hours, then cooled to room temperature. This was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution. The aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, then the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=93:7) to obtain the entitled compound (87 mg, 58%) as a white solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionThe aqueous layer was further extracted twice with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe insoluble matter was separated by filtration
  6. customthe solvent was evaporated away
  7. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=93:7)

Quellen und Nachweise

ORD-Eintrag
ord-83b49c662a0d43a68d7ccfa72e4a7ba5
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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