Pyridine → N-(2-Acetyl-5-methoxyphenyl)-2-((1-methylethyl)amino)-4-thiazolecarboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 46 (4.4 g, 16.5 mmol) and the aniline derivative 93 (2.75 g, 16.5 mmol) in pyridine (140 mL) was cooled to −30° C. (upon cooling, the clear solution became partially a suspension). POCl3 (3.3 mL, 35 mmol) was added slowly over a 5 min period. The mixture was stirred at −30° C. for 1 h, and was then allowed to assume rt. After stirring at rt for 1.5 h the reaction mixture was poured over ice, and the pH was adjusted to about 9-10 using solid and saturated NaHCO3. The crude product was extracted into CH2Cl2 (3×) and the combined organic phases were dried (MgSO4) and evaporated. The crude dark-beige solid was purified by flash column chromatography (hexane/EtOAc 55:45) to give compound 47 (5.6 g, 76%) as a pale yellow solid.

Provenance & Evidence