Réaction #44475

Équation de réaction

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

2-amino-5-methylthiazole

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

sodium carbonate

→

title compound

Rendement 14.0%

N-(4-(6-(5-methylthiazol-2ylamino)pyrazin-2-ylthio)phenyl)cyclopropanecarboxamide

Rendement 14.0%

Solvants

ethyl acetate

Water

1,4-dioxan

Conditions de réaction

Traitement

1. 1
   Autrethe layers separated
2. 2
   ExtractionThe aqueous layer was extracted further with ethyl acetate (2×10 mL)
3. 3
   Séchagethe combined organic layers dried (MgSO4)
4. 4
   Concentrationconcentrated in vacuo
5. 5
   AutreThe residue was purified by column chromatography
6. 6
   Lavageeluting with MeOH:CH2Cl2 (1:20)

Mode opératoire

To a solution of N-(4-(6-chloropyrazin-2-ylthio)phenyl)cyclopropanecarboxamide (0.82 mmol) and 2-amino-5-methylthiazole (0.86 mmol) in 1,4-dioxan (3 mL), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.05 mmol), tris(dibenzylideneacetone)dipalladium (0.03 mmol) and sodium carbonate (1.15 mmol) were added. The resulting solution was heated at 120° C. in the microwave (175 W, 25 psi) for 3 h. 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 eluting with MeOH:CH2Cl2 (1:20) to give the title compound (42.5 mg, 14%) as a light brown solid; 1H NMR (400 MHz, DMSO-d6) δ 0.81 (4H, m), 1.82 (1H, m), 2.16 (3H, s), 3.32 masked signal, 6.99 (1H, m), 7.58 (2H, m), 7.76 (2H, m), 7.84 (1H, s), 8.04 (1H, s), 10.49 (1H, s), 11.50 (1H, br s); MS (ES+): m/e=384.48 (100%).

Source