2-Aminothiazole → HCID 10066302, compound

Participants

Reaction Conditions

Reaction Steps

A solution of triphenylphosphine (355 mg, 1.35 mmol) in methylene chloride (3 mL) cooled to 0° C. was treated with N-bromosuccinimide (240 mg, 1.35 mmol). The reaction was stirred at 0° C. for 15 min. At this time, the reaction was treated with 6-chloro-1-pentyl-1H-indole-3-carboxylic acid (300 mg, 1.13 mmol). The reaction was stirred at 0° C. for 10 min and then was allowed to warm to 25° C. where it was stirred for 1 h. The reaction was then treated with 2-aminothiazole (283 mg, 2.83 mmol) and stirred at 25° C. for 3 d. At this time, the reaction was partitioned between water (50 mL) and ethyl acetate (50 mL). This mixture was treated with a 10% aqueous hydrochloric acid solution (15 mL), shaken, and separated. The organic layer was washed with a saturated aqueous sodium bicarbonate solution (1×30 mL), water (1×30 mL), and a saturated aqueous sodium chloride solution (1×30 mL). The organic layer was then dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 2/1 hexanes/ethyl acetate) afforded 6-chloro-1-pentyl-1H-indole-3-carboxylic acid thiazol-2-ylamide (101 mg, 25%) as a pink solid: mp 139-141° C.; EI-HRMS m/e calcd for C17H18ClN3OS (M+) 347.0859, found 347.0859.

Provenance & Evidence