4-Bromoaniline → HCID 13221932, Verbindung

HRID 1472821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1472821
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N:9]1([CH:14]([CH3:18])[C:15](O)=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC(N(C)C)=O.O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:15](=[O:16])[CH:14]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH3:18])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 78074-BromoanilineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 31571772-(Pyrrolidin-1-yl)propanoic acid

Produkt 1

HCID 13221932HCID 13221932, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

4-Bromo aniline (0.25 g, 1.45 mmol), 2-pyrrolidin-1-ylpropanoic acid (0.25 g, 1.74 mmol) and diisopropylethylamine (0.3 ml, 1.74 mmol) were dissolved in dimethylacetamide (5 ml). HBTU (0.66 g, 1.74 mmol) was subsequently added and the mixture was stirred overnight. The reaction mixture was added to water and extracted twice with ethyl acetate. The combined organics were washed several times with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the desired product. Yield: 0.43 g, 100%. LCMS method: 2, RT: 2.73 min; MI: 297-299 [M+1].

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organics were washed several times with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e7f9a3d3964f49e3aff55599e70f4088
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012633B2

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