Binap, (A+-)- → 5-((5-Chloro-4-((1-methylpiperidin-4-yl)amino)pyridin-2-yl)amino)pyrazine-2-carbonitrile

HRID 384678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384678
[Cl:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.Br[C:18]1[C:23]([C:24]#[N:25])=[N:22][CH:21]=[CH:20][N:19]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>O1CCOCC1>[Cl:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[CH:4][C:5]([NH:8][C:20]2[N:19]=[CH:18][C:23]([C:24]#[N:25])=[N:22][CH:21]=2)=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 596134945-Chloro-N4-(1-methylpiperidin-4-yl)pyridine-2,4-diamineHCID 626739383-Bromopyrazine-2-carbonitrile

Produkt 1

HCID 596134475-((5-Chloro-4-((1-methylpiperidin-4-yl)amino)pyridin-2-yl)amino)pyrazine-2-carbonitrileAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of 5-chloro-N4-(1-methylpiperidin-4-yl)pyridine-2,4-diamine (0.080 g, 0.33 mmol), 2-bromo-cyanopyrazine (0.040 g, 0.22 mmol), BINAP (0.005 g, 0.02 mmol), sodium tert-butoxide (0.030 g, 0.31 mmol), tris(dibenzylideneacetone)dipalladium chloroform complex (0.009 g, 0.01 mmol) in dioxane (1.6 mL) was stirred at r.t. under nitrogen for 10 min before being heated under microwave irradiation for 30 min at 90° C. The crude reaction mixture was purified by ion exchange on SCX-II acidic resin (1 g) eluting with methanol/dichloromethane (1/1), then 2M ammonia-methanol. The basic fractions were combined and the solvent was removed in vacuo. The crude mixture was purified by preparative thin layer chromatography eluting with methanol/dichloromethane (1/9) to give the title compound as a yellow solid (0.023 g, 30%).

Aufarbeitung

  1. customThe crude reaction mixture
  2. customwas purified by ion exchange on SCX-II acidic resin (1 g)
  3. washeluting with methanol/dichloromethane (1/1)
  4. customthe solvent was removed in vacuo
  5. customThe crude mixture was purified by preparative thin layer chromatography
  6. washeluting with methanol/dichloromethane (1/9)

Quellen und Nachweise

ORD-Eintrag
ord-58472639952b4bf490ebd769b27ccba5
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367658B2

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