Pyridine → HCID 86644710, Verbindung

HRID 455246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455246
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([O:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([NH:23][C:24](=[O:36])[CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=4)[CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.N1C=CC=CC=1.[CH:43]1([C:46](Cl)=[O:47])[CH2:45][CH2:44]1>O1CCCC1.C(OCC)(=O)C>[CH:43]1([C:46]([NH:1][C:2]2[S:3][C:4]3[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([O:15][C:16]4[CH:21]=[CH:20][C:19]([F:22])=[C:18]([NH:23][C:24](=[O:36])[CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[CH:27]=5)[CH:17]=4)[CH:8]=[CH:7][C:5]=3[N:6]=2)=[O:47])[CH2:45][CH2:44]1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 86644709HCID 86644709, Verbindung

Produkt 1

HCID 86644710HCID 86644710, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-amino-6-[4-fluoro-3-({[3-(trifluoromethyl)phenyl]acetyl}amino)phenoxy]-1,3-benzothiazole-7-carboxylate (2.50 mg, 4.81 mmol) in tetrahydrofuran (20 mL) were added pyridine (770 μL, 9.62 mmol) and cyclopropanecarbonyl chloride (790 μL, 8.66 mmol), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate (80 mL), washed successively with saturated aqueous sodium hydrogen carbonate solution (50 ml) and saturated brine (50 mL), and the organic layer was dried over anhydrous magnesium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=40/60→80/20), and a fraction containing the object product was concentrated under reduced pressure. The obtained pale-yellow residue was recrystallized from ethyl acetate/n-hexane (3/2) to give the title compound (2.25 g, 80%) as a white powder.

Aufarbeitung

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate solution (50 ml) and saturated brine (50 mL)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationInsoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=40/60→80/20)
  6. additiona fraction containing the object product
  7. concentrationwas concentrated under reduced pressure
  8. customThe obtained pale-yellow residue was recrystallized from ethyl acetate/n-hexane (3/2)

Quellen und Nachweise

ORD-Eintrag
ord-6db517c7415f4e7f91b8c2cb255f353d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497274B2

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