Benzoyl chloride, 3-chloro- → HCID 71238641, Verbindung

HRID 1846658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846658
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([NH2:18])=[CH:16][C:15]([C:19]#[N:20])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)[CH3:2].[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>C(#N)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[C:17]([NH:18][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][CH:31]=[C:23]([Cl:22])[CH:24]=3)=[CH:16][C:15]([C:19]#[N:20])=[CH:14][N:13]=2)[CH2:10][CH2:11]1)[CH3:2]

Komponenten

4

Edukt 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 68303889HCID 68303889, Verbindung

Produkt 1

HCID 71238641HCID 71238641, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 0.043 g (0.15 mol) of (3′-amino-5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid ethyl ester in acetonitrile (3 mL) is added 0.021 mL (0.16 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred at room temperature for 2 hours then concentrated under reduced pressure. The residue is taken up in a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The combined organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to give 0.047 g (73%) of [3′-(3-chloro-benzoylamino)-5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester as a light yellow solid.

Aufarbeitung

  1. concentrationthen concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c8505327a13d4bcfa7ead8bf20e3146f
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952004B2

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