Sodium Hydroxide → 1-[5-[7-Bromo-2-(ethylcarbamoylamino)-6-methoxy-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid

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Reaction Conditions

Reaction Steps

Ethyl 1-[5-[7-bromo-2-(ethylcarbamoylamino)-6-methoxy-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (47 mg, 0.081 mmol) was dissolved in EtOH (3 mL) and NaOH solution (1 mL, 1 M, aq) was added to give a pale yellow solution. The mixture was heated to 60° C. overnight then cooled to rt, the EtOH removed under reduced pressure and the residue acidified with HCl solution (1 M, aq) to pH 3. The mixture was extracted into EtOAc (3×15 mL) and the combined organic layer washed with brine, dried over Na2SO4 and concentrated to dryness under reduced pressure. The mixture was purified by chromatography, Biotage SP4, 4 g Si cartridge, 50-100% EtOAc in heptane. The relevant fractions were combined to give Compound 208 as an off white solid, 8 mg (18%). 1H NMR (CDCl3): δ 1.31 (3H, t, J=7.2 Hz), 1.42 (3H, s), 1.61 (2H, m), 2.27 (2H, m), 3.47 (2H, m), 3.64 (3H, s), 3.84 (2H, m), 4.15 (2H, q, J=7.2 Hz), 4.2-7.2 (3H, br s), 7.48 (1H, s), 8.62 (2H, s). MS: 549.07/551.06 [M+H]+.

Provenance & Evidence