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Dimethylformamide → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1-phenylpyrrolidine-3-carboxamide

HRID 58692
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 58692
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH2:14].CN(C(ON1N=N[C:25]2[CH:26]=CC=N[C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:39]([N:42]([CH2:46][CH3:47])[CH:43]([CH3:45])[CH3:44])([CH3:41])C.CN([CH:51]=[O:52])C>>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH:14][C:51]([CH:47]1[CH2:41][CH2:39][N:42]([C:43]2[CH:44]=[CH:26][CH:25]=[CH:24][CH:45]=2)[CH2:46]1)=[O:52]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 66832116N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1-phenylpyrrolidine-3-carboxamide
Ausbeute 18 %

Versuchsvorschrift

A mixture of the intermediate 60 (1-(4-cyanophenyl)-2-oxopyrrolidine-3-carboxylic acid) (0.124 g, 0.649 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.150 g; 0.649 mmol), HATU (0.271 g; 0.713 mmol) and N,N-diisopropylethylamine (0.280 mL; 1.62 mmol) in DMF (3 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulphate and the organic layer was successively washed with sodium carbonate, brine, dried and evaporated to dryness. The crude mixture was purified by crystallization from a mixture of dichloromethane and methanol to afford 0.044 g (18%) of the desired compound as a white solid.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulphate
  2. washthe organic layer was successively washed with sodium carbonate, brine
  3. customdried
  4. customevaporated to dryness
  5. customThe crude mixture was purified by crystallization from a mixture of dichloromethane and methanol

Quellen und Nachweise

ORD-Eintrag
ord-e5f2621262414921a9457fa50b470017
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09434722B2

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