Hydrochloric Acid → HCID 178492641, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-cyclopropyl-8-methoxyimidazo[1,2-a]pyridin-6-carboxylate (30 mg, 0.122 mmol) was dissolved in THF (1.5 mL) and MeOH (1.5 mL), and added by aqueous 5 N sodium hydroxide solution (0.12 mL, 0.609 mmol), then stirred at 60° C. for 2 hours. This was cooled to room temperature, added by 5 N hydrochloric acid (0.12 mL, 0.609 mL), concentrated under reduced pressure, and then azeotroped with toluene. The residue was dissolved in DMF (2 mL) and water (0.5 mL), and 6-(1H-tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (47 mg, 0.146 mmol), triethylamine (0.026 mL, 0.183 mmol), HOBT (25 mg, 0.183 mmol) and EDCI HCl (35 mg, 0.183 mol) were added thereto. The reaction mixture was stirred at 90° C. for 2 hours, then cooled to room temperature, and water was added thereto. The precipitated solid was collected by filtration, and dried under reduced pressure to obtain the intended compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.42 (1H, s), 8.24 (1H, d, J=8.5 Hz), 8.19 (1H, s), 7.33 (1H, d, J=8.5 Hz), 7.30 (1H, s), 6.68 (1H, s), 4.50-3.20 (5H, m), 3.95 (3H, s), 2.98 (2H, s), 2.10-1.80 (4H, m), 1.03-0.96 (2H, m), 0.69-0.64 (2H, m); MS [M+H]+=500.

Provenance & Evidence