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Imidazole → HCID 10000618, Verbindung

HRID 490265
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 490265
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20](Br)[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH:32]1[CH:36]=[CH:35][N:34]=[CH:33]1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([N:32]1[CH:36]=[CH:35][N:34]=[CH:33]1)[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 8471TriethylamineHCID 210970583-Benzyl-2-(1-bromo-2-methylpropyl)-7-chloroquinazolin-4(3H)-one

Produkt 1

HCID 10000618HCID 10000618, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysator
HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of (±)-3-benzyl-2-(1-bromo-2-methyl-propyl)-7-chloro-3H-quinazolin-4-one (a compound of Formula 105, 250 mg, 0.616 mmol) in DMF (3 mL) was added triethylamine (0.130 mL, 0.924 mmol) and imidazole (63.0 mg, 0.924 mmol) followed by tetrabutylammonium iodide (228 mg, 0.616 mmol). The resultant solution was heated to 90° C., stirred for 18 h and allowed to cool to room temperature. The reaction mixture was quenched with water (3 mL) and diluted with ether (10 mL). The aqueous layer was extracted with ether (10 mL) ad the combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (1:1 hexanes:ethyl acetate) to provide 38 mg (16%) of the title compound as a yellow solid. MS(ES+) m/e 393.0 [M+H]+.

Aufarbeitung

  1. customThe reaction mixture was quenched with water (3 mL)
  2. additiondiluted with ether (10 mL)
  3. extractionThe aqueous layer was extracted with ether (10 mL) ad the combined extracts
  4. dry with materialwere dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (1:1 hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ed32b4add5b64d8b8e50b0a685c5a26a
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07528137B2

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