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

HRID 17458
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17458
[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]([CH:14]=[CH2:15])[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]([CH:14]=[CH2:15])[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 685849162-Cyclopropyl-7-fluoro-5-methyl-6-vinyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 510421142-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-vinyl-1,3-benzoxazole-4-carbonitrileAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-Cyclopropyl-7-fluoro-5-methyl-6-vinyl-1,3-benzoxazole-4-carbonitrile (I-180) (100 mg, 0.41 mmol) was dissolved in dimethyl sulfoxide (2 ml), then at room temperature, triethylamine (86 μl, 0.62 mmol) and (3S)-3-(dimethylamino)pyrrolidine (68 μl, 0.54 mmol) were added. The solution was stirred under nitrogen atmosphere at 90° C. for 4.5 hours. After cooling to room temperature, the reaction liquid 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=9:1) to obtain a roughly-purified product (123 mg, 89%) as a pale brown solid. This was recrystallized from diisopropyl ether and hexane to obtain the entitled compound (79 mg) as a white solid.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe reaction liquid
  3. extractionThe aqueous layer was further extracted twice with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-acbba13ed54f4c7aba590ad90c9d1f0e
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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