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Oxalyl chloride → (E)-4-Methyl-1-[(1S,4S)-5-(2-methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pent-2-en-1-one

HRID 1775343
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1775343
[CH3:1][CH:2]([CH3:8])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:16][C:17]1[C:22]([N:23]2[CH2:28][C@@H:27]3[CH2:29][C@H:24]2[CH2:25][NH:26]3)=[CH:21][CH:20]=[CH:19][N:18]=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:26]1[CH2:25][C@@H:24]2[CH2:29][C@H:27]1[CH2:28][N:23]2[C:22]1[C:17]([CH3:16])=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:7]
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Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 6420393-Isopropyl acrylic acidHCID 89825789(1S,4S)-5-(2-Methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane hydrochloride

Produkt 1

HCID 89833044(E)-4-Methyl-1-[(1S,4S)-5-(2-methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pent-2-en-1-oneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(E)-4-Methylpent-2-enoic acid (57 mg, 0.5 mmol) was dissolved in dichloromethane (2 ml), oxalyl chloride (42 μl, 0.5 mmol) 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 (1S,4S)-5-(2-methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane hydrochloride (66 mg, 0.3 mmol) in DCM (2 ml). DIPEA (175 μl, 1 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 59 mg of a solid (0.21 mmol, 69%).

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-e86a41553aad451bb37bb53a37198cbb
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09260441B2

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