Hydrochloric Acid → HCID 67265781, compound

Participants

Reaction Steps

A solution of {4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzoylamino}-acetic acid ethyl ester (105 mg, 230 μmol) in 2 M LiOH in methanol (10 mL) is stirred at rt for 20 h. The mixture is acidified by adding aq. HCl before it is extracted twice with EA. The aq. solution is neutralised by adding sat. aq. NaHCO3 solution and concentrated. The remaining solid is suspended in methanol, filtered and the filtrate is concentrated. The remaining residue is again suspended in a small volume of methanol, filtered and the filtrate is again concentrated. The crude product is purified by CC on silica gel eluting with DCM containing 20% of methanol to give the title compound (30 mg) as a white solid; LC-MS: tR=0.48 min; [M+1]+=429.09; 1H NMR (D6-DMSO): δ1.04 (t, J=7.0 Hz, 6H), 2.23 (s, 3H), 2.58 (q, J=7.3 Hz, 4H), 3.60 (d, J=4.8 Hz, 2H), 3.74 (s, 2H), 7.84 (s, 1H), 8.02-8.07 (m, 2H), 8.10-8.15 (m, 2H), 8.17 (t, J=4.5 Hz, 1H).

Provenance & Evidence