Hydrochloric Acid → HCID 71547822, compound

Participants

Reaction Steps

To a stirred solution of ethyl 4-(6-(1-(1H-imidazol-1-yl)propyl)pyridin-3-yl)benzoate (25 mg, 0.07 mmol; prepared as described in Example 5) in THF (2 mL) and water (1 mL) was added LiOH (6 mg, 0.14 mmol) at rt and the reaction was stirred at rt for about 4 h. The reaction mixture was neutralized with 1N HCl (pH=6) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), the organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by prep TLC using 5% methanol in DCM to provide 4-(6-(1-(1H-imidazol-1-yl)propyl)pyridin-3-yl)benzoic acid as an off white solid (12 mg, 54.5% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.92 (s, 1H), 8.14 (dd, 1H), 8.01 (d, 2H), 7.83 (d, 3H), 7.40 (d, 1H), 7.31 (s, 1H), 6.90 (s, 1H), 5.39 (s, 1H), 2.34-2.19 (m, 2H), 0.81 (t, 3H), LC-MS m/z calcd for [M+H]+ 308.13. found 308.1.

Provenance & Evidence