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Diisopropylethylamine → HCID 86699393, Verbindung

HRID 1777556
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1777556
FC1C=C(N(C)[C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)C=CC=1.Cl.[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH2:30][CH2:31][NH2:32].CN(C(ON1N=N[C:43]2[CH:44]=[CH:45][CH:46]=N[C:42]1=2)=[N+](C)C)C.[F:50][P-](F)(F)(F)(F)F.C(N([CH2:64][CH3:65])C(C)C)(C)C>CN(C=O)C>[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH2:30][CH2:31][NH:32][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([CH2:42][C:43]2[CH:65]=[CH:64][CH:46]=[C:45]([F:50])[CH:44]=2)=[CH:17][CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 132411752-(5-bromo-1H-indol-3-yl)ethan-1-amine hydrochlorideHCID 61984652HCID 61984652, Verbindung

Produkt 1

HCID 86699393HCID 86699393, Verbindung
Ausbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-((3-fluorophenyl)(methyl)amino)benzoic acid (0.250 g, 1.09 mmol), 2-(5-bromo-1H-indol-3-yl)ethanamine hydrochloride (0.300 g; 1.09 mmol), HATU (0.414 g; 1.09 mmol) and N,N-diisopropylethylamine (0.469 mL; 2.72 mmol) in DMF (7 mL), was stirred at room temperature for 72 hours. The reaction mixture was then partitioned between ethyl acetate and sodium hydrogen sulfate and the organic layer was successively washed with a saturated aqueous solution of sodium carbonate and brine. The organic layer was dried, concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 1 to 20% ethyl acetate in dichloromethane) to afford 0.395 g (81%) of the title compound as a white solid.

Aufarbeitung

  1. customThe reaction mixture was then partitioned between ethyl acetate and sodium hydrogen sulfate
  2. washthe organic layer was successively washed with a saturated aqueous solution of sodium carbonate and brine
  3. customThe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customthe crude material was purified by flash chromatography on silica gel (eluent 1 to 20% ethyl acetate in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-f0c5dfb5f4844f5fbe3d0855ff3a9a81
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266832B2

Notizen zur Reaktion

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