2-Aminothiazole → HCID 9927282, compound

A solution of 3-cyclopentyl-2-(4-ethynyl-phenyl)-propionic acid (121 mg, 0.50 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (332 mg, 0.75 mmol), triethylamine (0.21 mL, 1.50 mmol) and 2-aminothiazole (86 mg, 0.75 mmol) in methylene chloride (5 mL) was stirred at 25° C. for 24 h. At this time, the reaction was diluted with methylene chloride (10 mL). This solution was 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). The aqueous layers were back extracted with methylene chloride (1×10 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-ethynyl-phenyl)-N-thiazol-2-yl-propionamide (92 mg, 56.8%) as a white solid: mp 181-183° C.; EI-HRMS m/e calcd for C19H20N2OS (M+) 324.1296, found 324.1295.

1. washThis solution was washed with water (1×10 mL)
2. extractionThe aqueous layers were back extracted with methylene chloride (1×10 mL)
3. dry with materialThe combined organic extracts were dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo

ORD record

ord-b26c528550904dd7abfabc74335b79a0

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06388071B2