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Trifluoroacetic acid → HCID 86732400, Verbindung

HRID 517275
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 517275
Br[CH2:2][C:3]([O:5]C(C)(C)C)=[O:4].[O:10]=[C:11]1[NH:20][CH:19]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][C:22]=2[S:29]([CH3:32])(=[O:31])=[O:30])[C:18]2[C:17](=[O:33])[CH2:16][CH2:15][CH2:14][C:13]=2[N:12]1[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)C(O)=O>CN(C)C=O.O>[C:25]([C:24]1[CH:27]=[CH:28][C:21]([CH:19]2[C:18]3[C:17](=[O:33])[CH2:16][CH2:15][CH2:14][C:13]=3[N:12]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:42])([F:43])[F:41])[CH:35]=3)[C:11](=[O:10])[N:20]2[CH2:2][C:3]([OH:5])=[O:4])=[C:22]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:23]=1)#[N:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetate2×HCID 867323284-(1-(3-(Trifluoromethyl)phenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile

Produkt 1

HCID 86732400HCID 86732400, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

tert-Butyl bromoacetate (200 L, 1.35 mmol) is added to a mixture of 4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile (example 18, 440 mg, 0.90 mmol) and cesium carbonate (440 mg, 1.35 mmol) in N,N-dimethylformamide (5 mL), and the mixture is stirred at room temperature for 3 h. Another portion of tert-butyl bromoacetate (200 μL, 1.35 mmol) is added, and the mixture is stirred for 2 h. Water is added, and the mixture is extracted with ethyl acetate. The phases are separated and the organic layer is concentrated under reduced pressure. The residue is dissolved in acetonitrile (3 mL), and the mixture is treated with trifluoroacetic acid (10 mL, 123 mmol) and stirred at room temperature for 6 h. All volatiles are removed under reduced pressure, and the residue is directly used in the next step without further purification. Yield: 460 mg.

Aufarbeitung

  1. stirringthe mixture is stirred for 2 h
  2. extractionthe mixture is extracted with ethyl acetate
  3. customThe phases are separated
  4. concentrationthe organic layer is concentrated under reduced pressure
  5. dissolutionThe residue is dissolved in acetonitrile (3 mL)
  6. stirringstirred at room temperature for 6 h
  7. customAll volatiles are removed under reduced pressure
  8. customthe residue is directly used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-c9ab0f120b1b43be9c326979d821d688
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09115093B2

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