Hydrochloric Acid → 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanoic acid hydrochloride

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A solution of methyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanoate formic acid salt (Preparation 6, 5.9 mg, 0.0132 mmol) and LiOH (0.15 mg) in THF-MeOH-water (300 μl, 300 μl, 100 μl) was irradiated to 100° C. for 3 min in the microwave. 2M aqueous HCl (1 ml) and DCM (2 ml) were added sequentially, and a precipitate formed. Filtration gave the title compound as a white solid (6.5 mg, quant.). 1H NMR (400 MHz, d6-DMSO) δ 12.71 (1H, br s), 11.41 (1H, br s), 8.53 (1H, d), 8.41 (1H, dd), 8.05 (1H, d), 7.57 (1H, d), 7.53 (1H, t), 7.46 (1H, d), 4.99 (1H, sept), 4.53 (2H, br s), 3.46-3.43 (4H, m), 3.65 (2H, br s), 2.98 (2H, t), 1.39 (6H, d); m/z (ES) 433 [M+H+].

Provenance & Evidence