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Water → 1-{5-[4-(5-Cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-4-methylpyridin-2-yl}pyrrolidin-2-one

HRID 2411723
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2411723
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[CH:9]1([C:12]2[CH:13]=[C:14]([CH3:34])[C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([C:26]4[CH:27]=[N:28][C:29](F)=[CH:30][C:31]=4[CH3:32])=[O:25])[CH2:20][CH2:19]3)=[N:16][CH:17]=2)[CH2:11][CH2:10]1.O>CN(C)C=O>[CH:9]1([C:12]2[CH:13]=[C:14]([CH3:34])[C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([C:26]4[C:31]([CH3:32])=[CH:30][C:29]([N:3]5[CH2:7][CH2:6][CH2:5][C:4]5=[O:8])=[N:28][CH:27]=4)=[O:25])[CH2:20][CH2:19]3)=[N:16][CH:17]=2)[CH2:10][CH2:11]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 58484562HCID 58484562, Verbindung

Produkt 1

HCID 712519061-{5-[4-(5-Cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-4-methylpyridin-2-yl}pyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

Under a nitrogen stream, sodium hydride (47 mg) was suspended in N,N-dimethylformamide (10 mL), pyrrolidin-2-one (74 μL) was added, and the mixture was stirred at room temperature. Then, a solution of [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl](6-fluoro-4-methylpyridin-3-yl)methanone (210 mg) described in Preparation Example 140 in N,N-dimethylformamide (5 mL) was added, and the mixture was stirred at 95° C. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography to give 1-{5-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-4-methylpyridin-2-yl}pyrrolidin-2-one. The obtained 1-{5-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-4-methylpyridin-2-yl}pyrrolidin-2-one was dissolved in dichloromethane, 1N hydrogen chloride/diethyl ether (5 mL) was added, and the precipitate was collected by filtration to give the title compound (12 mg).

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was stirred at 95° C
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aabd3470558b42c594246f2b683d988d
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08816079B2

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