Hydrochloric Acid → HCID 49806787, compound

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Reaction Steps

3-Bromo-4-tert-butyl-benzoyl chloride was prepared according to general procedure B from 3-bromo-4-tert-butyl-benzoic acid (500 mg) and used without further purification. 3-Bromo-4-tert-butyl-benzoyl chloride (295 mg, 1.07 mmol) was stirred in acetone (5 mL) and sodium thiocyanate (87 mg, 1.07 mmol) added to give a red-orange suspension which was stirred at room temperature for 16 h. A solution of 5-dimethylamino-pentanoic acid (4-amino-phenyl)-amide (4, prepared as described above) in acetone (5 mL) was added and the yellow suspension stirred for a further 16 h. The reaction mixture was diluted in dichloromethane and filtered to give a crude mixture which was purified by column chromatography eluting with methanol/dichloromethane (0% to 20%) to give 5-dimethylamino-pentanoic acid {4-[3-(3-bromo-4-tert-butyl-benzoyl)-thioureido]-phenyl}-amide as a yellow solid. The hydrochloride salt was prepared by dissolving the amine in a minimal volume of acetone (1-2 mL) and adding 2 M hydrochloric acid in diethyl ether (200 μL). The resulting solid was filtered to give 5-dimethylamino-pentanoic acid {4-[3-(3-bromo-4-tert-butyl-benzoyl)-thioureido]-phenyl}-amide hydrochloride (50 mg) as a yellow solid.

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