p-Toluenesulfonic acid → 3-cyclopentyl-3-(4-(2-(4-(4-(methylsulfonyl)piperazin-1-yl)phenylamino)pyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1876858Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876858
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:14][C:15]#[N:16])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[N:22]1([C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C1(C)C=C[C:38]([S:41](O)(=[O:43])=[O:42])=CC=1.C(=O)([O-])[O-].[Na+].[Na+].CS(Cl)(=O)=O>O1CCOCC1.O>[CH:17]1([CH:13]([N:11]2[CH:12]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:32][C:31]4[CH:33]=[CH:34][C:28]([N:22]5[CH2:23][CH2:24][N:25]([S:41]([CH3:38])(=[O:43])=[O:42])[CH2:26][CH2:27]5)=[CH:29][CH:30]=4)[N:7]=3)[CH:9]=[N:10]2)[CH2:14][C:15]#[N:16])[CH2:21][CH2:20][CH2:19][CH2:18]1

Komponenten

8

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 4229251-(4-Aminophenyl)piperazineHCID 866372883-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile

Produkt 1

HCID 580146523-cyclopentyl-3-(4-(2-(4-(4-(methylsulfonyl)piperazin-1-yl)phenylamino)pyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 3-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile (30 mg, 0.1 mmol), 4-(piperazin-1-yl)aniline (28.5 mg, 0.149 mmol), and p-toluenesulfonic acid (14 mg, 0.084 mmol) in dry 1,4-dioxane (0.8 mL) was refluxed overnight, then cooled to room temperature. To the resulting mixture was added 1.0 M sodium carbonate in water (0.8 mL), followed by methanesulfonyl chloride (0.015 mL, 0.20 mmol). The reaction was stirred at room temperature for 30 min and the phases were separated. The organic phase was purified on RP-HPLC at pH 10 to give the desired product as a racemic mixture (33 mg, 63%). LCMS (M+H) 521.1.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. customthe phases were separated
  3. customThe organic phase was purified on RP-HPLC at pH 10

Quellen und Nachweise

ORD-Eintrag
ord-77d16fafda214554ab5b38a1dfce2400
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309718B2

Notizen zur Reaktion

Wird geladen…