Reaktion #44476

Reaktionsgleichung

N-(4-(6-chloropyrazin-2-ylthio)phenyl)cyclopropanecarboxamide

3-amino-5-methylpyrazole

4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

sodium carbonate

→

title compound

Ausbeute 6.0%

N-(4-(6-(3-methyl-1H-pyrazol-5-ylamino)pyrazin-2-ylthio)phenyl)cyclopropanecarboxamide

Ausbeute 6.0%

Lösungsmittel

ethyl acetate

Water

1,4-dioxan

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe layers separated
2. 2
   ExtraktionThe aqueous layer was extracted further with ethyl acetate (2×10 mL)
3. 3
   Trocknenthe combined organic layers dried (MgSO4)
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe residue was purified by column chromatography (EtOAc/Petroleum ether, 0-100% gradient EtOAc)
6. 6
   Sonstigepurified further
7. 7
   SonstigeHPLC purification (sunfire C18 column, trifluoroacetic acid/MeCN/MeOH as eluent)

Vorschrift

To a solution of N-(4-(6-chloropyrazin-2-ylthio)phenyl)cyclopropanecarboxamide (0.49 mmol) and 3-amino-5-methylpyrazole (0.52 mmol) in 1,4-dioxan (3 mL), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.03 mmol), tris(dibenzylideneacetone) dipalladium (0.02 mmol) and sodium carbonate (0.69 mmol) were added. The resulting solution was heated at 120° C. in the microwave (175 W, 25 psi) for 30 min. Water (10 mL) and ethyl acetate (10 mL) were added and the layers separated. The aqueous layer was extracted further with ethyl acetate (2×10 mL), the combined organic layers dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/Petroleum ether, 0-100% gradient EtOAc) and then purified further using mass directed HPLC purification (sunfire C18 column, trifluoroacetic acid/MeCN/MeOH as eluent) to give the title compound (10.6 mg, 6%) as a light yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 0.81 (4H, m), 1.83 (1H, m), 2.05 (3H, s), 5.55 (1H, s), 7.54 (2H, m), 7.59 (1H, s), 7.74 (2H, m), 8.02 (1H, s), 9.77 (1H, s), 10.47 (1H, s); MS (ES+): m/e=367.41 (100%).

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