Hydrochloric Acid → HCID 69457310, compound

Participants

Reaction Steps

To a solution of 3-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-(methyl)ethylamino]ethyl}-1H-indole-7-carboxylic acid (29.1 mg, 0.0821 mmol) in N,N-dimethylformamide (3 mL) are added ethylamine hydrochloride (67 mg, 0.822 mmol), triethylamine (171 μL, 1.23 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (WSCI) hydrochloride (78.7 mg, 0.411 mmol) and 1-hydroxybenzotriazole (HOBt, 55.5 mg, 0.411 mmol), and the mixture is stirred at room temperature for 17 hours. The reaction solution is poured into a saturated aqueous sodium hydrogen carbonate solution, and the mixture is separated into chloroform. The organic layer is washed with a saturated brine and dried over anhydrous sodium sulfate. The solvent is removed by distillation, and the resulting crude product is purified by preparative TLC (a saturated ammonia solution in chloroform:methanol=20:1) to give 3-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-(methyl)ethyl-amino]ethyl}-1H-indole-7-carboxylic acid ethylamide (7.5mg, 0.0197 mmol, 24%).

Provenance & Evidence