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Oxalyl chloride → (E)-4-Methyl-1-[4-(4-methyl-2-pyridyl)-1,4-diazepan-1-yl]pent-2-en-1-one

HRID 1775337
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Reaktionsgleichung

Reaktionsgleichung von HRID 1775337
[CH3:1][CH:2]([CH3:8])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.Cl.Cl.[CH3:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([N:24]2[CH2:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:19]=1.CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C>[CH3:8][CH:2]([CH3:1])/[CH:3]=[CH:4]/[C:5]([N:27]1[CH2:28][CH2:29][CH2:30][N:24]([C:20]2[CH:19]=[C:18]([CH3:17])[CH:23]=[CH:22][N:21]=2)[CH2:25][CH2:26]1)=[O:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 6420393-Isopropyl acrylic acidHCID 898257101-(4-Methylpyridin-2-YL)-1,4-diazepane dihydrochloride

Produkt 1

HCID 89833066(E)-4-Methyl-1-[4-(4-methyl-2-pyridyl)-1,4-diazepan-1-yl]pent-2-en-1-oneAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(E)-4-Methylpent-2-enoic acid (26 mg, 0.23 mmol) was dissolved in dichloromethane (1 ml), oxalyl chloride (20 μl, 0.23 mol) and one drop of DMF were added and the resulting solution was stirred at room temperature for 15 minutes. This solution was added to a solution of 1-(4-methyl-2-pyridyl)-1,4-diazepane dihydrochloride (40 mg, 0.15 mmol) in DCM (2 ml). DIPEA (80 μl, 0.5 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 13 mg of a solid (0.047 mmol, 20%).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-7fa755bc4e834191879b744c5d0d06cf
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09260441B2

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