2-Aminothiazole → Rac-2-cyclopentyloxy-2-(3,4-dichloro-phenyl)-n-thiazol-2-yl-acetamide

Temperature

25 °C

A solution of rac-cyclopentyloxy-(3,4-dichloro-phenyl)-acetic acid (52 mg, 0.17 mmol) in dichloromethane (10 mL) was treated with O—(1H-benzotriazolo-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) (72 mg, 0.19 mmol), diisopropyl-ethylamine (0.09 mL, 0.52 mmol) and 2-aminothiazole (26 mg, 0.25 mmol). The resulting brownish-orange solution was then stirred 16 h at 25° C. The reaction was then diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with water (1×10 mL), 1N sodium hydroxide solution (1×10 mL), 1N hydrochloric acid (1×10 mL) and brine (1×10 mL), then were dried over sodium sulfate and concentrated in vacuo. The product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate) to furnish rac-2-cyclopentyloxy-2-(3,4-dichloro-phenyl)-N-thiazol-2-yl-acetamide (45 mg, 70% yield) as a white foam: EI-HRMS m/e calcd for C16H16Cl2O2N2S (M+) 370.0309, found 370.0309.

1. extractionextracted with ethyl acetate (3×15 mL)
2. washThe combined organic layers were washed with water (1×10 mL), 1N sodium hydroxide solution (1×10 mL), 1N hydrochloric acid (1×10 mL) and brine (1×10 mL)
3. dry with materialwere dried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate)

ORD record

ord-454df27118d14b0e874448347d72b337

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608218B2