Hydrochloric Acid → HCID 68891892, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (5 N) (0.44 mmol, 0.1 mL) was added to a solution of ethyl 3-(4-(5-(3-cyano-4-isopropylthiophenyl)-1,3,4-thiadiazol-3-yl)-3-methylphenyl)propanoate (0.09 mmol, from Step D) in ethanol (2 mL). The reaction mixture was stirred at 50° C. for 1 h. The reaction was acidified to a pH<7 with 2 N HCl and the product was extracted with EtOAc (20 mL). The organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with 10% methanol/methylene chloride yielded 12 mg of the title compound: 1H NMR (500 MHZ, CDCl3) δ 8.26 (s, 1H), 8.24 (d, J=8.3, H), 7.74 (d, J=7.7, 1H), 7.62 (d, J=8.3, 1H), 7.28 (s, 1H), 7.24 (d, J=8.0, 1H), 3.70-3.78 (m, 1H), 3.02-3.10 (m, 2H), 2.76-2.82 (m, 2H), 2.68 (s, 3H), 1.47 (d, J=6.4, 6H); ESI-MS (m/z) 423.9; HPLC A: 3.79 min.

Provenance & Evidence