2-Aminothiazole → HCID 10000140, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3,4-dichloro-phenyl)-3-(tetrahydro-pyran-2-yl)-propionic acid (81 mg, 0.27 mmol) in N,N-dimethylformamide (5 mL) was treated with O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (112 mg, 0.29 mmol), N,N-diisopropylethylamine (0.14 mL. 0.80 mmol), and 2-aminothiazole (40 mg, 0.40 mmol). The reaction was stirred at 25° C. for 16 h. At this time, the reaction was diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with water (1×10 mL), a 1N aqueous sodium hydroxide solution (1×10 mL), a 1N aqueous hydrochloric acid solution (1×10 mL), and a saturated aqueous sodium chloride solution (1×10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 90/10 hexanes/ethyl acetate to 60/40 hexanes/ethyl acetate) afforded 2-(3,4-dichloro-phenyl)-3-(tetrahydro-pyran-2-yl)-N-thiazol-2-yl-propionamide (35 mg, 34%) as a light yellow oil: EI-HRMS m/e calcd for C17H18Cl2N2O2S (M+) 384.0466, found 384.0468.

Provenance & Evidence