Tert-Butylamine → 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid tert-butylamide

Participants

Reaction Steps

To a solution of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid (prepared as in Example 3, 240 mg, 0.58 mmol) and tert-butylamine (122 μL, 1.16 mmol) in dichloromethane (4 mL), N,N-dimethylformamide (500 μL) and N-methylmorpholine (160 μL, 1.55 mmol) was added 1-hydroxybenzotriazole hydrate (132 mg, 0.97 mmol) followed by N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (186 mg, 0.97 mmol) in one portion at room temperature. The resulting mixture was stirred for 14 h. The mixture was diluted with ethyl acetate (100 mL), washed with a 1N aqueous sodium bicarbonate solution, 1 N aqueous hydrochloric acid solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid tert-butylamide (280 mg, quant.) as a light yellow solid which was used without further purification: LC/MS m/e calcd for C26H33N3O3S [M+H]+ 468.64, observed 467.8.

Provenance & Evidence