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p-Toluenesulfonic acid → Azd3463

HRID 1256054
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1256054
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[C:5]([Cl:17])=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]2)=[CH:21][C:20]=1[O:32][CH3:33].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)CCCC>[NH2:31][CH:28]1[CH2:29][CH2:30][N:25]([C:22]2[CH:23]=[CH:24][C:19]([NH:18][C:2]3[N:7]=[C:6]([C:8]4[C:16]5[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=5)[NH:10][CH:9]=4)[C:5]([Cl:17])=[CH:4][N:3]=3)=[C:20]([O:32][CH3:33])[CH:21]=2)[CH2:26][CH2:27]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 566553763-(2,5-Dichloropyrimidin-4-yl)-1H-indoleHCID 667101811-(4-Amino-3-methoxyphenyl)piperidin-4-amine

Produkt 1

HCID 56599293Azd3463Ausbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 62761-PentanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A solution of 3-(2,5-dichloropyrimidin-4-yl)-1H-indole (5.28 g, 20 mmol), 1-(4-amino-3-methoxyphenyl)piperidin-4-amine (4.43 g, 20.00 mmol), and tosic acid (5.71 g, 30.00 mmol) in n-pentanol (40.0 ml) was placed in a round-bottomed flask. The solution was heated at 140° C., and stirred at that temperature for three days. The solvent was removed by concentration in vacuo, and to the residue was added sat. NaHCO3 solution and dichloromethane. The mixture was filtered and the obtained solid was dissolved in a mixture of THF and methanol and pre-absorbed on silica gel (120 g). The mixture was loaded onto silica gel column and eluted with 10% MeOH, 1% NH4OH in DCM. The collected fractions were concentrated, and the residue was triturated in diethyl ether. The collected solid after filtration was triturated in ethanol. Filtration afforded the title compound (3.25 g, 36.2% yield).

Aufarbeitung

  1. customThe solvent was removed by concentration in vacuo
  2. additionto the residue was added sat. NaHCO3 solution and dichloromethane
  3. filtrationThe mixture was filtered
  4. dissolutionthe obtained solid was dissolved in a mixture of THF and methanol
  5. custompre-absorbed on silica gel (120 g)
  6. washeluted with 10% MeOH, 1% NH4OH in DCM
  7. concentrationThe collected fractions were concentrated
  8. customthe residue was triturated in diethyl ether
  9. filtrationThe collected solid after filtration
  10. customwas triturated in ethanol
  11. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-d8ff5d3cf85947279f0dfec98f6fb564
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08461170B2

Notizen zur Reaktion

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