Hydrochloric Acid → 2-[(1-Methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride

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Reaction Steps

A mixture of 1,1-dimethylethyl 5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 4; 53.7 mg, 0.117 mmol) and 4M HCl in dioxane (2 ml) was stirred at room temperature for 64 h. The mixture was concentrated in vacuo, the residue triturated with Et2O and dried in vacuo to leave a light brown solid (35.1 mg, 76%). 1H NMR (400 MHz, d6-DMSO) δ 9.52 (2H, br. s), 8.52 (1H, d), 8.40 (1H, dd), 8.02 (1H, dd), 7.57, (1H, d), 7.51-7.48 (2H, m), 4.99 (1H, sept.), 4.38 (2H, s), 3.39-3.34 (4H, m), 1.39 (6H, d); m/z (ES) 361 [M+H]+.

Provenance & Evidence