Hydrochloric Acid → HCID 68163486, compound

Participants

Reaction Steps

To a solution of 6-[2-(butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxylic acid (68 mg) in dichloromethane (1.8 mL) were successively added methanesulfonamide (19 mg), 4-dimethylaminopyridine (49 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (77 mg). This mixture was stirred for 62 hours at room temperature. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with dichloromethane. The organic layer was washed with 1 mol/L hydrochloric acid and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-methanol) to obtain the title compound (62 mg). 1H-NMR (DMSO-d6) δ ppm: 0.79 (3H, t, J=7.3 Hz), 1.19 (3H, d, J=6.9 Hz), 1.45-1.75 (2H, m), 2.80-2.95 (1H, m), 3.34 (3H, s), 3.83 (3H, s), 5.58 (2H, s), 6.32 (1H, s), 6.65-6.80 (1H, m), 7.20 (1H, s), 7.53 (1H, s), 7.85-7.95 (2H, m), 11.41 (1H, br s). ESI-MS (m/z): 450, 452 (M+H)+

Provenance & Evidence