Hydrochloric Acid → 1-{5-[7-Ethyl-2-(3-ethyl-ureido)-benzothiazol-5-yl]-pyrimidin-2-yl}-4-methyl-piperidine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

1-{5-[7-Ethyl-2-(3-ethyl-ureido)-benzothiazol-5-yl]-pyrimidin-2-yl}-4-methyl-piperidine-4-carboxylic acid ethyl ester (19 mg) was dissolved in EtOH (1 mL) and 1 M aq NaOH (1 mL) added. The mixture was stirred at 70° C. overnight. The mixture was cooled to rt and acidified to pH 3 with 1 M HCl (aq) then concentrated in vacuo and the residue suspended (sonication) in ˜10% MeOH in DCM. The mixture was filtered through a syringe filter (20 micron) and the filtrate concentrated in vacuo. A cream solid was obtained (54 mg) and purified by preperative HPLC (Gilson, 40s-70-100% water/MeCN+0.1% formic acid). The relevant fractions were combined and concentrated in vacuo slightly then freeze-dried to give Compound 37 (2 mg) as a white solid. 1H NMR (CDCl3+CD3OD): δ 1.21 (3H, t, J=7.2 Hz), 1.25 (3H, s), 1.35 (3H, t, J=7.6 Hz), 1.45 (2H, m), 2.17 (2H, br d, J=13.6 Hz), 2.85 (2H, q, J=7.6 Hz), 3.32-3.41 (4H, m), 4.31 (2H, br dt, J=13.8 and 4.0 Hz), 7.14 (1H, s), 7.54 (1H, s), 8.54 (1H, s), 8.54 (1H, s). m/z: 469 [M+H]+.

Provenance & Evidence