2-Aminothiazole → HCID 10020953, compound

Participants

Reaction Conditions

Reaction Steps

A solution of triphenylphosphine (377 mg, 1.44 mmol) in methylene chloride (4 mL) cooled to 0° C. was treated with N-bromosuccinimide (256 mg, 1.44 mmol). The reaction was stirred at 0° C. for 15 min. At this time, the reaction was treated with 1-isopropyl-6-trifluoromethyl-1H-indole-3-carboxylic acid (300 mg, 1.11 mmol). The reaction was stirred at 0° C. for 5 min and then was allowed to warm to 25° C. where it was stirred for 30 min. The reaction was then treated with 2-aminothiazole (255 mg, 2.54 mmol) and stirred at 25° C. for 24 h. At this time, the mixture was partitioned between water (50 mL) and ethyl acetate (50 mL) and treated with a 1N aqueous hydrochloric acid solution (25 mL). The organic layer was washed with a saturated aqueous sodium bicarbonate solution (1×25 mL) and a saturated aqueous sodium chloride solution (1×25 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, diethyl ether) afforded 1-isopropyl-6-trifluoromethyl-1H-indole-3-carboxylic acid thiazol-2-ylamide (43 mg, 11%) as a light pink solid: mp 246-247° C.; EI-HRMS m/e calcd for C16H14F3N3OS (M+) 353.0810, found 353.0801.

Provenance & Evidence