Trifluoroacetic acid → Sorafenib related compound 10

HRID 1184943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184943
[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 separsted 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 vacumn 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 organic phase was removed
  4. filtrationThe aqueous layer was filtered
  5. washthe solid was washed with water (30 mL×2)
  6. customThe solid was dried under vacumn

Quellen und Nachweise

ORD-Eintrag
ord-8cf10e22a5214a1e980186e7f998e615
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669369B2

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