Trifluoroacetic acid → Sorafenib related compound 10

HRID 1522921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522921
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[NH:10][C:11]2[CH:30]=[CH:29][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([O:24]C(C)(C)C)=[O:23])[CH:17]=3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:32]([F:35])([F:34])[F:33].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[NH:10][C:11]2[CH:30]=[CH:29][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([OH:24])=[O:23])[CH:17]=3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:32]([F:35])([F:33])[F:34]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57541570HCID 57541570, Verbindung

Produkt 1

HCID 59772925Sorafenib related compound 10Ausbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

At room temperature, tert-butyl 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)picolinate (1.4 g, 2.76 mmol) was dissolved in dichloromethane (20 mL). To the resulted solution, trifluoroacetic acid (20 mL) and triethylsilane (0.5 mL) were added. The resulted mixture was heated to 50° C. and stirred for 16 hours. The solvent was removed under reduced pressure, and water (50 mL) and ethyl acetate (70 mL) were added. The resulted mixture was separated and the organic phase was removed. The aqueous layer was filtered and the solid was washed with water (30 mL×2). The solid was dried under vacuum to give the title compound (1.1 g, purity 97%, yield 90%) as a light green solid.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure, and water (50 mL) and ethyl acetate (70 mL)
  2. additionwere added
  3. customThe resulted mixture was separated
  4. customthe organic phase was removed
  5. filtrationThe aqueous layer was filtered
  6. washthe solid was washed with water (30 mL×2)
  7. customThe solid was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1e94d92ce6f64588bbad6541f3c2e5ff
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09078933B2

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