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4-Methoxybenzylamine → (6-Amino-4-methylpyridin-3-yl) [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone

HRID 2411272
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2411272
[CH:1]1([C:4]2[CH:5]=[C:6]([CH3:26])[C:7]([N:10]3[CH2:15][CH2:14][N:13]([C:16]([C:18]4[CH:19]=[N:20][C:21](F)=[CH:22][C:23]=4[CH3:24])=[O:17])[CH2:12][CH2:11]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.COC1C=CC(C[NH2:34])=CC=1>O>[NH2:34][C:21]1[N:20]=[CH:19][C:18]([C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:7]3[C:6]([CH3:26])=[CH:5][C:4]([CH:1]4[CH2:3][CH2:2]4)=[CH:9][N:8]=3)[CH2:11][CH2:12]2)=[O:17])=[C:23]([CH3:24])[CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 754524-MethoxybenzylamineHCID 58484562HCID 58484562, Verbindung

Produkt 1

HCID 71252201(6-Amino-4-methylpyridin-3-yl) [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanoneAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl](6-fluoro-4-methylpyridin-3-yl)methanone (1.45 g) described in Preparation Example 140 and 4-methoxybenzylamine (1.12 g) was stirred at 100° C. for 5 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was dissolved in dichloromethane (10 mL), trifluoroacetic acid (20 mL) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (1.07 g).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. dissolutionThe obtained residue was dissolved in dichloromethane (10 mL)
  6. additiontrifluoroacetic acid (20 mL) was added
  7. stirringthe mixture was stirred at room temperature overnight
  8. additionWater was added to the reaction mixture
  9. extractionthe mixture was extracted with dichloromethane
  10. washThe organic layer was washed with saturated brine
  11. customthe solvent was evaporated
  12. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-eca8707fe8f84ae984fe16e8126d7604
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08816079B2

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