Diisopropylethylamine → HCID 66832008, Verbindung

HRID 58699

Reaktionsgleichung

Reaktionsgleichung von HRID 58699
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].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH3:57][O:58][C:59]1[CH:64]=[CH:63][C:62]([N:65]2[CH2:69][CH2:68][CH:67]([C:70](O)=[O:71])[C:66]2=[O:73])=[CH:61][CH:60]=1>CN(C=O)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:70]([CH:67]1[CH2:68][CH2:69][N:65]([C:62]2[CH:63]=[CH:64][C:59]([O:58][CH3:57])=[CH:60][CH:61]=2)[C:66]1=[O:73])=[O:71]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 33731171-(4-Methoxyphenyl)-2-oxo-3-pyrrolidinecarboxylic acid

Produkt 1

HCID 66832008HCID 66832008, VerbindungAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.098 g; 0.425 mmol), PyBOP (0.332 g; 0.638 mmol), N,N-diisopropylethylamine (0.220 mL; 1.28 mmol) and 1-(4-methoxyphenyl)-2-oxopyrrolidine-3-carboxylic acid (0.100 g; 0.425 mmol) was stirred in DMF (3 mL) overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate, the organic layer was washed with sodium carbonate, brine, dried and concentrated under reduced pressure. The crude mixture was purified flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.074 g (42%) of the title compound as a solid.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate
  2. washthe organic layer was washed with sodium carbonate, brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mixture was purified flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-20677edda8354cdea484ecb4305b8e5b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434722B2

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