N,N-Dimethylglycine → HCID 53250921, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of {2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-methanol (prepared as in Example 8, 30 mg, 0.075 mmol), dimethylamino-acetic acid (21 mg, 0.11 mmol) in N,N-dimethylformamide (1.0 mL) and N-methylmorpholine (33 uL, 0.23 mmol) was added 1-hydroxybenzotriazole hydrate (20 mg, 0.113 mmol) followed by N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (29 mg, 0.11 mmol) in one portion. The mixture was stirred at 25° C. for 6 h, 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 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 dimethylamino-acetic acid 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylmethyl-ester (20 mg, 54.9%) as a light yellow solid: LC/MS m/e calcd for C26H33N3O4S1 [M+H]+ 484.63, observed 484.3; 1H NMR (400 MHz, CDCl3) δ ppm 1.19 (m, 2H), 1.48 (m, 2H), 1.56-1.86 (m, 5H, H), 2.12 (m, 1H), 2.27 (m, 1H), 2.43 (s, 6H, 2×NCH3), 3.02 (s, 3H), 3.29 (s, 2H, NCH2), 4.28 (t, J=7.8 Hz, 1H), 5.28 (s, 2H), 6.38 (s, 1H), 7.50 (d, J=8.0 Hz, 2H), 7.87 (d, J=8.0 Hz, 2H), 7.39 (s, 1H), 8.16 (s, 1H), 10.87 (s, 1H).

Provenance & Evidence