2-Aminothiazole → HCID 1246351, compound

To a solution of (3,4-dichloro-phenyl)-acetic acid (500 mg, 2.4 mmol)in N,N-dimethylformamide (15 mL) at 25° C. was added HBTU (1.02 g, 2.7 mmol), 2-aminothiazole (360 mg, 3.6 mmol) and diisopropylethylamine (1.25 mL, 7.2 mmol). The reaction mixture was stirred for 16 h, then was diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed in turn with water (1×10 mL), 1N sodium hydroxide (1×10 mL), 1 N hydrochloric acid (1×10 mL) and brine (1×10 mL), then were dried over sodium sulfate, filtered and evaporated under reduced pressure. The residual material was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 50150 hexanes/ethyl acetate) to furnish rac-2-(3,4-dichloro-phenyl)-N-thiazol-2-yl-acetamide (480 mg, 70% yield) as a light yellow solid, mp 169.8-172.3° C. EI-HRMS m/e calcd for C11H8N2OSCl2 (M+) 285.9734, found 285.9734.

1. extractionextracted with ethyl acetate (3×15 mL)
2. washThe combined organic layers were washed in turn with water (1×10 mL), 1N sodium hydroxide (1×10 mL), 1 N hydrochloric acid (1×10 mL) and brine (1×10 mL)
3. dry with materialwere dried over sodium sulfate
4. filtrationfiltered
5. customevaporated under reduced pressure
6. customThe residual material was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 50150 hexanes/ethyl acetate)

ORD record

ord-f26d1fe4e9014e3e987d74e8c133247a

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608218B2