Ethanolamine → 2-[2-cyclopentyl-1-(6-methanesulfonyl-pyridin-3-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid(2-hydroxy-ethyl)-amide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[2-cyclopentyl-1-(6-methanesulfonyl-pyridin-3-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid (80 mg, 0.19 mmol) and 2-amino-ethanol (14 uL, 0.23 mmol) in dichloromethane (1 mL), N,N-dimethylformamide (1 mL) and N-methylmorpholine (60 uL, 0.58 mmol) was added 1-hydroxybenzotriazole hydrate (54 mg, 0.39 mmol), followed by N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (75 mg, 0.39 mmol) in one portion. The mixture was then stirred at 25° C. for 14 h. The mixture was diluted with ethyl acetate (100 mL), washed with a 1 N sodium bicarbonate solution, 1 N aqueous hydrochloric acid solution, brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-[2-cyclopentyl-1-(6-methanesulfonyl-pyridin-3-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid(2-hydroxy-ethyl)-amide (30 mg, 34%) as a white solid: LC/MS m/e calcd for C23H28N4O4S [M+H]+ 456.57, observed 457.0; 1H NMR (400 MHz, CDCl3) δ ppm 1.17 (m, 2H), 1.47 (m, 2H), 1.55-1.84 (m, 5H, H), 2.08 (m, 1H), 2.24 (m, 1H), 3.20 (s, 3H), 3.60 (m, 2H), 3.80 (m, 2H), 4.26 (m, 1H), 6.37 (s, 1H), 7.61 (br, 1 H), 7.85 (br, 1H), 7.97 (m, 1H), 8.29 (m, 1H), 8.59 (br. s., 1H), 8.63 (s, 1H), 11.01 (br, 0.2H).

Provenance & Evidence