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Triethylsilane → HCID 66614157, Verbindung

HRID 510137
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 510137
COC1C=C(OC)C=CC=1C[N:6]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][O:18][CH3:19])[C:12]2[C:7]1=[N:8][C:9]([C:20]1[C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[F:36])[N:21]=1)=[N:10][CH:11]=2.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[F:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][N:22]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:28]2[C:20]([C:9]2[N:8]=[C:7]3[C:12]([N:13]([CH2:16][CH2:17][O:18][CH3:19])[C:14](=[O:15])[NH:6]3)=[CH:11][N:10]=2)=[N:21]1
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Komponenten

4

Edukt 2

HCID 12052TriethylsilaneHCID 66614128HCID 66614128, Verbindung

Produkt 1

HCID 66614157HCID 66614157, VerbindungAusbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

317 mg (0.501 mmol) of the compound from example 83A were dissolved in 15 ml of trifluoroacetic acid, 582 mg (5.009 mmol) of triethylsilane were added and the mixture was heated to reflux for 18 h. The reaction mixture was partitioned between water and ethyl acetate, and neutralized with saturated aqueous sodium hydrogencarbonate solution. The organic phase was dried over sodium sulfate and concentrated on a rotary evaporator. The residue was dried under high vacuum. and purified by means of preparative HPLC (eluent: methanol/water with 0.1% trifluoroacetic acid, gradient 30:70→90:10). 167 mg of the title compound were obtained (79% of theory).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue was dried under high vacuum
  7. customand purified by means of preparative HPLC (eluent: methanol/water with 0.1% trifluoroacetic acid, gradient 30:70→90:10)

Quellen und Nachweise

ORD-Eintrag
ord-30536b820a0f4be8bd25b991470062f4
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09096592B2

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