Diisopropylethylamine → HCID 67331064, Verbindung

HRID 1896795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896795
[F:1][C:2]([F:8])([F:7])[CH2:3][C:4](O)=[O:5].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:42]1([C:48]2[O:49][C:50]3[CH:56]=[CH:55][C:54]([NH2:57])=[CH:53][C:51]=3[CH:52]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>ClCCl.C(OCC)(=O)C>[C:42]1([C:48]2[O:49][C:50]3[CH:56]=[CH:55][C:54]([NH:57][C:4](=[O:5])[CH2:3][C:2]([F:8])([F:7])[F:1])=[CH:53][C:51]=3[CH:52]=2)[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 27779723,3,3-Trifluoropropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 167651722-Phenyl-1-benzofuran-5-amine

Produkt 1

HCID 67331064HCID 67331064, VerbindungAusbeute 29,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 3,3,3-trifluoropropanoic acid (136 mg, 1.06 mmol) in dry dichloromethane (10 mL) was added HATU (468 mg, 1.23 mmol) and diisopropylethylamine (580 μL, 3.35 mmol). The mixture was then stirred at room temperature for 10 min. 2-phenylbenzofuran-5-amine (234 mg, 1.12 mmol) was then added and the resulting mixture was stirred at room temperature for 48 h. Ethyl acetate was added and the organic layer was washed once with saturated aqueous water. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting using a gradient (ethyl acetate/hexanes 1:3 v/v to ethyl acetate/hexanes 1:1 v/v) followed by trituration in ethyl acetate to afford 99.3 mg (28%) of the title compound (LCMS RT=6.62 min)

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 48 h
  2. washthe organic layer was washed once with saturated aqueous water
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. customevaporated
  5. customThe resulting solid was purified by column chromatography
  6. washeluting

Quellen und Nachweise

ORD-Eintrag
ord-07da71ba7d574f3cbd8def2a87ffe4a8
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518980B2

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